СПЕКТРОСКОПИЧЕСКИ И/ИЛИ СТРУКТУРНО ИНТРИГУЮЩИЕ ФТАЛОЦИАНИНЫ И РОДСТВЕННЫЕ СОЕДИНЕНИЯ. ЧАСТЬ 1. МОНОМЕРНЫЕ СИСТЕМЫ

  • Nagao Kobayashi Университет Шиншу
Ключевые слова: порфирин, фталоцианин, структура, спектроскопия, расчеты молекулярных орбиталей (МО)

Аннотация

Представлена первая часть серии обзорных работ по свойствам некоторых синтетически и спектроскопически интересных исследований нашей группы за период 2007-2017 гг. В частности, приведены примеры анализа спектроскопических данных в сочетании с расчетами методом молекулярных орбиталей. Мы использовали в основном спектроскопические методы электронного поглощения и естественного и магнитного кругового дихроизма, периодически применяя флуоресценцию, фосфоресценцию и ЭПР с временным разрешением. Теоретически проанализированы спектры (4n + 2) p систем, а также некоторые 4np антиароматических систем, что помогает читателю интерпретировать спектральные данные. В первой части и второй частях этого обзора рассматриваются мономерные системы, а в третьей - тримерные и тетрамерные системы.

. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .

Литература

Broun A., Tcherniac J. Uber die Produkte der Einwirkung von Acetanhydrid auf Phthalamid. Ber. Deut. Chem. Ges. 1907. V. 40. P. 2709-2714.

Kobayashi N. Synthesis, Optical Properties, Structures, and Molecular Orbital Calculations of Subazaporphyrin, Sub-phthalocyanine, Subnaphthalocyanines, and Related Com-pounds. J. Porphyrins and Phthalocyanines. 1999. V. 3. P. 453-467.

Kobayashi N. Phthalocyanines. Current Opinion in Solid State & Materials Science. 1999. V. 4. P. 345-353.

Kobayashi N. Phthalocyaninato Macrocyclic Molecules-Macromolecules Applied in Various Fields. Kagaku to Kogyou (Chemistry and Industry). 1999. V. 52. P. 968-971.

Ishii K., Kobayashi N. The Excited Multiplet States of Met-alloporphyrins and Metallophthalocyanines Coordinated or Linked to Nitroxide Radicals. Coord. Chem. Rev. 2000. V. 198. P. 231-250.

Kobayashi N., Konami H. Molecular Orbitals and Electronic Spectra of Benzo-Fused and Related Porphyrin Analogues. J. Porphyrins and Phthalocyanines. 2001, V. 5, P. 233-255.

Kobayashi N. Optically Active Phthalocyanines. Coord. Chem. Rev. 2001. V. 221/222. P. 99-123.

Kobayashi N. Dimers, Trimers, and Oligomers of Phthalocy-anines and Related Compounds. Coord. Chem. Rev. 2002. V. 227. P. 129-152.

Kobayashi N. Design, Synthesis, Structure, and Spectro-scopic and Electrochemical Properties of Phthalocyanines. Bull. Chem. Soc. Jpn. (Accounts) 2002. V. 75. P. 1-19.

Kobayashi N. Porphyrins and Phthalocyanines as They are (in Japanese). Bull. Jpn. Soc. Coord. Chem. 2002. V. 39. P. 26-30.

Kobayashi N., Leznoff C.C. Synthesis, Structure and Prop-erties of New Phthalocyanines. J. Porphyrins and Phthalocy-anines. 2004. V. 8. P. 1015-1019.

Kobayashi N. Metal Complexes of Macrocyclic π Systems (in Japanese). Kagaku to Kyouiku (Chemistry and Education). 2004. V. 52. P. 28-29.

Kobayashi N., Fukuda T. Leading-Edge Research on Phthalocyanines (in Japanese). Kagaku Kougyou (Chemical Industry). 2004. V. 55. P. 771-777.

Muranaka, A., Okuda M., Kobayashi N. Recognition of Chiral Catechols Using Oxo-Titanium Phthalocyanine (in Jap-anese). Shokuhin-Shokuhin Tenkabutsu Kenkyushi (Foods & Food Ingredients J. Jpn). 2005. V. 210. P. 849-853.

Kobayashi N., Muranaka A. High Precision Analysis of Molecular Electronic Structures of Organic Molecules by CD and MCD Spectroscopy. Yuki Gousei Kagaku Kyoukaishi (Journal of Synthetic Organic Chemistry, Japan). 2006. V. 64. P. 735-743.

Mack J., Stillman M. J., Kobayashi N. Application of MCD Spectroscopy to Porphyrinoids. Coord. Chem. Review. 2007. V. 251. P. 429-453.

Kobayashi N., Nakai K. Applications of Magnetic Circular Dichroism Spectroscopy to Porphyrins and Phthalocyanines. Chem. Commun. (Feature Article). 2007. P. 4077-4092.

Fukuda T., Kobayashi N. Hydrogenated Tetraazaporphyrins - Old but New Core-Modified Phthalocyanine Analogues. Dalton Trans. (Perspective). 2008. P. 4685-4704.

Kobayashi N., Fukuda T. Phthalocyanine, Porphyrin, Cy-clodextrin, and Polymer Systems Suitable for Studying by Circular Dichroism, Magnetic Circular Dichroism, and/or Electrochemistry. Bull. Chem. Soc. Jpn. (Award Account). 2009. V. 82. P. 631-663.

Shimizu S., Kobayashi N. Porphyrin Analogues that Realize Higher Oxidation State of Central Metal. Kagaku (Chemistry). 2009. V. 64. P. 64-65.

Yoshimoto S., Kobayashi N. Supramolecular Nanostruc-tures of Phthalocyanines and Porphyrins at Surfaces Based on the “Bottom-up Assembly”. Structure and Bonding. 2010. V. 135. P. 137-168.

Mack J., Kobayashi N. Low Symmetry Phthalocyanines and Their Analogues. Chem. Rev. 2011. V. 111. P. 281-321.

Shimizu S., Kobayashi N. Structurally-Modified Subphthal-ocyanines: Molecular Design towards Realization of Expected Properties from the Electronic Structure and Structural Fea-tures of Subphthalocyanine. Chem. Commun. (feature arti-cle). 2014. V. 50. P. 6949-6966.

Furuyama T., Kobayashi N. Design, Synthesis, and Proper-ties of Azaporphyrin Phosphorus Complexes. Yuki Gousei Kagaku Kyoukaishi (Journal of Synthetic Organic Chemistry, Japan). 2015. V. 73. P. 833-843.

Kobayashi N. Properties of Phthalocyanines and Porphyrins Deduced from Their Molecular Orbitals. Gendai Kagaku (Chemistry of Present Days), Tokyo Kagaku Dojin. 2016. V. 539. P. 30-35.

Lu H., Kobayashi N. Optically Active Porphyrin and Phthalocyanine Systems. Chem. Rev. 2016. V. 116. P. 6184-6261.

Hoshi H., Kobayashi N. Spectroscopic and Structural Prop-erties of Phthalocyanines Deduced from Their Frontier Mo-lecular Orbitals (MOs) and MO Calculations. Coord. Chem. Rev. 2017. V. 345. P. 31-41.

Furuyama T., Kobayashi N. Azaporphyrin Phosphorus(V) Complexes: Synthesis, Structure, and Modification of Optical Properties. PCCP. 2017. V. 19. P. 15596-15612.

Kobayashi N. Synthesis and Spectroscopic Properties of Phthalocyanine Analogues. In “Phthalocyanines-Properties and Applications”. Ed by C.C. Leznoff and A.B.P. Lever. V. II. Chap. 3 (pp. 97-161). New York, Weinheim, Cambridge: VCH. 1992.

Kobayashi N., Konami H. Electronic Spectra and Molecular Orbitals of Phthalocyanines. In“Phthalocyanines - Properties and Applications”. Ed by C.C. Leznoff and A.B.P. Lever. V. IV. Chap. 6 (pp. 343-404). New York, Weinheim, Cam-bridge: VCH. 1996.

Kobayashi N. Synthesis of Starting Materials of Phthalocya-nines and Metal-Free Phthalocyanines. In “Phthalocyanine-Kagaku to Kinou- (Phthalocyanines-Chemistry and Func-tions)”. Ed. by N. Kobayashi, H. Shirai. Sections 1.1 and 1.2 (pp. 1-20). Tokyo: IPC. 1997. (in Japanese).

Kobayashi N. Synthesis of Starting Materials of Phthalocya-nine Congeners. In “Phthalocyanine-Kagaku to Kinou- (Phthalocyanines-Chemistry and Functions)”. Ed. by N. Ko-bayashi and H. Shirai. Section 1.4 (pp. 28-39). Tokyo: IPC. 1997. (in Japanese).

Kobayashi N. Synthesis of Phthalocyanine Congeners. In “Phthalocyanine-Kagaku to Kinou- (Phthalocyanines-Chemistry and Functions)”. Ed. by N. Kobayashi and H. Shi-rai. Section 1.5 (pp. 39-45). Tokyo: IPC. 1997. (in Japanese).

Koyama T., Shirai H., Kobayashi N. Langmuir and Blodgett Films of Phthalocyanines. In “Phthalocyanine-Kagaku to Kinou- (Phthalocyanines-Chemistry and Func-tions)”. Ed. by N. Kobayashi, H. Shirai. Section 2.5 (pp. 108-119). Tokyo: IPC. 1997. (in Japanese).

Kobayashi N. Electrochemistry of Phthalocyanines. In “Phthalocyanine-Kagaku to Kinou- (Phthalocyanines-Chemistry and Functions)”. Ed. by N. Kobayashi, H. Shirai. Section 4.1.1 (pp. 183-196). Tokyo: IPC. 1997. (in Japanese).

Kobayashi N. Phthalocyanine as Electrocatalysts. In “Phthal-ocyanine-Kagaku to Kinou- (Phthalocyanines-Chemistry and Functions)”. Ed. by N. Kobayashi, H. Shirai. Section 5.2 (pp. 290-301). Tokyo: IPC. 1997. (in Japanese).

Kobayashi N. meso-Azaporphyrins and Their Analogues. In “Handbook of Porphyrins and Related Macrocycles”. Ed. by K.M. Kadish, K.M. Smith, R. Guilard. V. 2. Chap. 13 (pp. 301-360). New York: Academic Press. 1999.

Kobayashi N. Synthesis and Spectroscopic Properties of Phthalocyanine Analogues. In “Handbook of Porphyrins and Related Macrocycles”. Ed. by by K.M. Kadish, K.M. Smith, R. Guilard. V. 15. Chap.100 (pp. 161-262). New York: Aca-demic Press. 2002.

Ishii K., Kobayashi N. The Photophysical Properties of Phthalocyanines and Related Compounds. In “Handbook of Porphyrins and Related Macrocycles”. Ed. by K.M. Kadish, K.M. Smith, R. Guilard. V. 16. Chap. 102 (pp. 1-42). New York: Academic Press. 2002.

Kobayashi N., Fukuda T. Phthalocyanines. In “Lecture on Experimental Chemistry”. Ed. by Chem. Soc. of Jpn. V. 22. Section 3.3.5 (pp. 452-460). Tokyo: Maruzen. 2004. (in Japa-nese).

Fukuda T., Kobayashi N. Deformed Phthalocyanines. In “Phthalocyanines as Functional Dyes”. Ed by R. Hirohashi, K. Sakamoto, E. Okumura. Section 2.4.3 (pp. 68-70). Tokyo: IPC. 2004. (in Japanese).

Fukuda T., Kobayashi N. Chemical Structure of Phthalocy-anines. In “Phthalocyanines as Functional Dyes”. Ed by R. Hirohashi, K. Sakamoto, E. Okumura. Section 3.1 (pp. 79-103). Tokyo: IPC. 2004. (in Japanese).

Ishii K., Kobayashi N. Electronic Structure and Photophysi-cal Properties of Phthalocyanines. In “Phthalocyanines as Functional Dyes”. Ed by R. Hirohashi, K. Sakamoto, E. Okumura. Sections 3.2 and 3.3 (pp. 103-122). Tokyo: IPC. 2004. (in Japanese).

Ishii K., Kobayashi N. Solid State Spectra of Phthalocya-nines. In “Phthalocyanines as Functional Dyes”. Ed by R. Hi-rohashi, K. Sakamoto, E. Okumura. Section 4.3 (pp. 199-204). Tokyo: IPC. 2004. (in Japanese).

Fukuda T., Kobayashi N. Magnetic Circular Dichroism Spectra of Phthalocyanines. In “Phthalocyanines as Functional Dyes”. Ed by R. Hirohashi, K. Sakamoto, E. Okumura. Sec-tion 4.4 (pp. 204-219). Tokyo: IPC. 2004. (in Japanese).

Kobayashi N., Yoshimoto Y. Electrochemistry and Electron Transfer of Phthalocyanines. In “Phthalocyanines as Func-tional Dyes”. Ed by R. Hirohashi, K. Sakamoto, E. Okumura. Chapter 7 (pp. 279-293). Tokyo: IPC. 2004. (in Japanese).

Kobayashi N., Fukuda T. Phthalocyanine as Pigments. In “Bunsan Gijutsu Daizenshu”. Section 4.6 (pp. 172-180). To-kyo: Joho Kikou. 2005. (in Japanese).

Kobayashi N., Fukuda T. Recent Progress in Phthalocya-nine Chemistry: Synthesis and Chacterization. In “Functional Dyes”. Ed by S. –H. Kim. Chap. 1 (pp. 1-47). Holland: Else-vier. 2005.

Kobayashi N. Progress in Phthalocyanine Synthesis. In “カラーフィルターにおける新しい材料開発と製造プロセス全集”. Section 1.1 (pp. 3-23). Tokyo: Technical Infor-mation Institute. 2006. (in Japanese).

Kobayashi N. Oxygen Electrocatalysis. In “Encyclopedia of Electrochemistry”. Ed by A.J. Bard, M. Stratman. V. 10 (Modified Electrode). Chap. 1 (pp. 687-694). Wiley-VCH. 2007.

Kobayashi N. Electrochromism. In “Inorganic Chemotro-pism”. Ed. by Y. Fukuda. Chap. 7 (pp. 291-336). Tokyo, Heidelberg: Kodansha, Splinger. 2007.

Kobayashi N. Metallophthalocyanines. In “Kinousei Shikiso no Gousei to Ouyou (Synthesis and Applied Technology of Functional Dyes)”. Ed. by M. Matsui. Chap. 4 (pp. 61-75). Tokyo: CMC. 2007. (in Japanese).

Kobayashi N. Optically Active Porphyrin Systems Analyzed by Circular Dichroism. In “Handbook of Porphyrin Science”. Ed. by K.M. Kadish, K.M. Smith, R. Guilard. V. 7. Chap. 33 (pp. 147-245). Singapore: World Scientific. 2010.

Fukuda T., Kobayashi N. Electronic Absorption Spectra – Phthalocyanines. In “Handbook of Porphyrin Science”. Ed. by K.M. Kadish, K.M. Smith, R. Guilard. V. 9. Chap. 42 (pp. 1-650). Singapore: World Scientific. 2010.

Mack J., Kobayashi N. Recent Applications of MCD Spec-troscopy to Porphyrinoids. In “Multiporphyrin Arrays”. Ed. by D. Kim Chapter 3 (pp. 91-147). Pan Stanford Publ. 2012.

Mack J., Kobayashi N., Shen Z. The Effect of Structural Modifications on the Properties of Porphyrinoids. In: “Hand-book of Porphyrin Science”. Ed. by K.M. Kadish, K.M. Smith, R. Guilard. Singapore: World Scientific. 2012. V. 23. Chapt. 109. P. 281-371.

Snow A.W. Phthalocyanine Aggregation. In “Handbook of Porphyrin Science”. Ed. by K.M. Kadish, K.M. Smith, R. Guilard. V. 23, Chap. 109 (pp. 281-371). Singapore: World Scientific. 2012.

Kobayashi N. Synthesis and Characterization of Chiral Phthalocyanines. In “Handbook of Porphyrin Science”. Ed. by K.M. Kadish, K. M. Smith, R. Guilard. V. 23. Chap. 110 (pp. 373-440). Singapore: World Scientific. 2012.

Kobayashi N. Muranaka A., Mack J. Circular Dichroism and Magnetic Circular Dichroism for Organic Chemists (text-book). London: Royal Society of Chemistry. 2012. (com-ments in Angew. Chem. Int. Ed. 2012, V. 51, P. 10446).

Kobayashi N. Porufirin oyobi Futaroshianin kei Shikiso (Porphyrinoid and Phthalocyaninoid Dyes). In “Kinou kei Shikiso no Kagaku (Science of Functional Dyes)”. Ed by H. Nakasumi. Chap. 11. pp. 157-172. Tokyo: Kagakudojin. 2013.

Shimizu S., Kobayashi N. Creation of Novel Pi-Electron Systems Based on Phthalocyanines, In ”Shinki Pai Kukan no Souhatsu to Kinou Kaihatsu (Creation and Functional Devel-opment of Novel Pi-Electron Systems)”. Ed by T. Akaska, A. Osuka, S. Fukuzumi, H. Kandori, pp. 85-90. Tokyo: CMC. 2013.

Shimizu S., Kobayashi N. Recent Advances in the Chemis-try of Phthalocyanine as Functional Chromophores. In “Chemical Science of π-Electron Systems”. Ed by T. Akaska, A. Osuka, S. Fukuzumi, H. Kandori. pp. 273-291. Tokyo: Springer JP. 2015.

Kobayashi N., Mack J., Ishii K., Stillman M.J. Electronic Structure of Reduced Symmetry Peripheral Fused-Ring-Substituted Phthalocyanines. Inorg. Chem. 2000. V. 41. P. 5350-5363.

Miwa H., Ishii K., Kobayashi N. Electronic Structures of Zinc and Palladium Tetraazaporphyrin Derivatives Controlled by Fused Benzo Rings. Chem. Eur. J. 2004. V. 10.P. 4422-4435.

Ishii K., Itoya H., Miwa H., Fujitsuka M., Ito O., Koba-yashi N. Relationship between Symmetry of Porphyrinic π-Conjugated Systems and Singlet Oxygen (1Δg) Yields: Low Symmetry Tetraazaporphyrin Derivatives. J. Phys. Chem. A. 2005. V. 109. P. 5781-5787.

Miwa H., Makarova E.A., Ishii K., Luk'yanets E. A., Kobayashi N. Spectroscopy, Electrochemistry, and Molecu-lar Orbital Calculations of Metal-Free Tetraazaporphyrin, -chlorine, -bacteriochlorin, and -isobachteriochlorin. Chem. Eur. J. 2002. V. 8. P. 1082-1090.

Firey P.A., Ford W.E., Sounik J.R., Kenney M.E., Rodg-ers M.A.J. Silicon Naphthalocyanine Triplet State and Oxy-gen. A Reversible Energy-Transfer Reaction. J. Am. Chem. Soc. 1988. V. 110. P. 7626-7630.

Aoudia M., Cheng G., Kennedy V.O., Kenney M.E., Rodgers M.A.J. Synthesis of a Series of Octabutoxy- and Octabutoxybenzophthalocyanines and Photophysical Proper-ties of Two Members of the Series. J. Am. Chem. Soc. 1997. V. 119. P. 6029-6039.

Ishii K., Takeuchi S., Shimizu S., Kobayashi N. A Con-cept for Controlling Singlet Oxygen (1Δg) Yields Using Ni-troxide Radicals: Phthalocyaninatosilicon Covalently Linked to Nitroxide Radicals. J. Am. Chem. Soc. 2004. V. 126. P. 2082-2088.

Turro N.J. Modern Molecular Photochemistry. Mill Valley, California: University Science Books. 1991.

Ishii, K., Kobayashi N. The Photophysical Properties of Phthalocyanines and Related Compounds. In “The Porphyrin Handbook”. Ed. by K.M. Kadish, R.M. Smith, R. Guilard. New York: Academic Press. 2003. V. 16. Chap. 102.

van der Waals J.H., van Dorp W.G., Schaafsma T.J. In The Porphyrins. Ed. by D. Dolphin. New York: Academic Press. 1978. V. 4. Chap. 3.

van Dorp W.G., Schoemaker W.H., Soma M., van der Waals J.H. The Lowest Triplet State of Free Base Porphyrin. Mol. Phys. 1975. V. 30. P. 1701-1721.

Ishii K., Ishizaki T., Kobayashi N. Experimental Evidence for a Selection Rule of Intersystem Crossing to the Excited Quartet States: Metallophthalocyanines Coordinated by 4-Amino-TEMPO. J. Phys. Chem. A. 1999. V. 103. P. 6060-6062.

Ishii K., Abiko S., Kobayashi N. Time-Resolved Electron Spin Resonance of Gallium and Germanium Porphyrins in the Excited Triplet State. Inorg. Chem. 2000. V. 39. P. 468-472.

Kobayashi N., Togashi M., Osa T., Ishii K., Yamauchi S., Hino H. Low Symmetrical Phthalocyanine Analogues Substi-tuted with Three Crown Ether Voids and Their Cation-Induced Supermolecules. J. Am. Chem. Soc. 1996. V. 118. P. 1073-1085.

Ishii K., Hirose Y., Kobayashi N. Selective Populations from the Excited Multiplet States to the Triplet Ground State in a Phthalocyanine: A New Concept for Controlling Magnet-ic Properties by Photoexcitation. J. Am. Chem. Soc. 1998. V. 120. P. 10551-10552.

Furuya F., Ishii K., Kobayashi N. Direct EPR Observations of Both Oxidized and Reduced Porphyrin Dimers in the Low-est Excited States: A Novel Analysis of a Homobiradical with a Strong Antiferromagnetic Interaction. J. Am. Chem. Soc. 2002. V. 124. P. 12652-12653.

Nakai K., Kurotobi K., Osuka A., Uchiyama M., Koba-yashi N. Electronic structures of azulene-fused porphyrins as seen by magnetic circular dichroism and TD-DFT calcula-tions. J. Inorg. Biochem. 2008. V. 102. P. 466-471.

Gouterman M. In The Porphyrins. Ed. by D. Dolphin. New York: Academic Press. 1978. V. 3. Chap. 1.

Michl J. Magnetic Circular Dichroism of Cyclic. Pi.-electron Systems. 1. Algebraic Solution of the Perimeter Model for the A and B Terms of High-Symmetry Systems with a (4N+2) π-Electron [n] Annulene Perimeter. J. Am. Chem. Soc. 1978. V. 100. P. 6801-6811.

Michl J. Magnetic Circular Dichroism of Cyclic. Pi.-electron Systems. 2. Algebraic Solution of the Perimeter Model for the B Terms of Systems with a (4N +2) π-Electron [n] Annulene Perimeter. J. Am. Chem. Soc. 1978. V. 100. P. 6812-6818.

Muranaka A., Homma S., Maeda H., Furuta H., Koba-yashi N. Detection of unusual ΔHOMO < ΔLUMO relation-ship in tetrapyrrolic cis- and trans-doubly N-confused porphy-rins. Chem. Phys. Lett. 2008. V. 460. P. 495-498.

Srinivasan A., Furuta H. Confusion Approach. to Porphy-rinoid Chemistry. Acc. Chem. Res. 2005. V. 38. P. 10-20.

Furuta H., Maeda H., Osuka A. Doubly N-Confused Por-phyrin: A New Complexing Agent Capable of Stabilizing Higher Oxidation States. J. Am. Chem. Soc. 2000. V. 122. P. 803-807.

Maeda H., Osuka A., Furuta H. Trans Doubly N-Confused Porphyrins: Cu(III) Complexation and Formation of Rodlike Hydrogen-Bonding Networks. J. Am. Chem. Soc. 2003. V. 125. P. 15690-15691.

Shimizu S., Haseba Y., Yamazaki M., Kumazawa G., Kobayashi N. Control of Chromophore Symmetry by Posi-tional Isomerism of Peripheral Substituents. Chem. Eur. J. 2014. V. 20. P. 4822-4828.

Furuyama T., Yoshida T., Hashizume D., Kobayashi N. Phosphorus(V) tetraazaporphyrins: Porphyrinoids Showing an Exceptionally Strong CT Band between the Soret and Q bands. Chem. Sci. 2014. V. 5. P. 2466-2474.

Kobayashi N., Nakajima S., Osa T. Spectroscopy, Electro-chemistry, and Spectroelectrochemistry of Tetra-tert-Butylated and Octaphenylated Tetraazaporphyrins. Chem. Lett. 1992. P. 2415-2418.

Fukuda T., Masuda S., Kobayashi N. Tetraazachlorin-Fullerene Conjugates: On-Off Control of Electronic Commu-nication Enabled by Push-Pull Substituents. J. Am. Chem. Soc. 2007. V. 129. P. 5472-5479.

Wu F., Liu J., Mishra P., Komeda T., Mack J., Chang Y., Kobayashi N., Shen Z. Modulation of the Molecular Spintronic Properties of Adsorbed Copper Corroles. Nature Commun. 2015. V. 6. 7547. DOI: 10.1038/ncomms8547.

Rocha A.R., García-Suárez V.M., Bailey S.W., Lambert C.J., Ferrer J., Sanvito S. Towards Molecular Spintronics. Nat. Mater. 2005. V. 4. P. 335–339.

Irie M. Photochromism: memories and switches introduction. Chem. Rev. 2000. V. 100. P. 1683–1684.

Yamase T. Photo- and Electrochromism of Polyoxometalates and Related Materials. Chem. Rev. 1998. V. 98. P. 307–326.

Vincent R., Klyatskaya S., Ruben M., Wernsdorfer W., Balestro F. Electronic Read-Out of a Single Nuclear Spin Us-ing a Molecular Spin Transistor. Nature. 2012. V. 488. P. 357–360.

Chang Y., Chen H., Zhou Z., Zhang Y., Schutt C., Her-ges R., Shen Z. A 20π-electron Heteroporphyrin Containing a Thienopyrrole Unit. Angew. Chem. Int. Ed. 2012, V. 124. P. 12973–12977.

Ghosh A., Wondimagegn T., Parusel A.B. Electronic Structure of Gallium, Copper, and Nickel Complexes of Cor-role. High-Valent Transition Metal Centers versus Non-Innocent Ligands. J. Am. Chem. Soc. 2000. V. 122. P. 5100–5104.

Bro ̈ring M., Bregier F., Consul Tejero E., Hell C., Hol-thausen M.C. Revisiting the Electronic Ground State of Copper Corroles. Angew. Chem. Int. Ed. 2007. V. 46. P. 445–448.

Alemayehu A.B., Gonzalez E., Hansen L. K., Ghosh A. Copper Corroles are Inherently Saddled. Inorg. Chem. 2009. V. 48. P. 7794–7799.

Pierloot K., Zhao H., Vancoillie S. Copper Corroles: The Question of Noninnocence. Inorg. Chem. 2010. V. 49. P. 10316–10329.

Kondo J. Effect of Ordinary Scattering on Exchange Scatter-ing from Magnetic Impurity in Metals. Phys. Rev. 1968. V. 169. P. 437–440.

Fano U. Effects of Configuration Interaction on Intensities and Phase Shifts. Phys. Rev. 1961. V. 124. P. 1866–1878.

Kobayashi N., Lever A.B.P. Cation or Solvent-Induced Supermolecular Phthalocyanine Formation: Crown Ether Sub-stituted Phthalocyanines. J. Am. Chem. Soc. 1987. V. 109. P. 7433–7441.

Kadish K.M., Adamian V.A., Caemelbecke E.V., Gueletii E., Will S., Erben C., Vogel E. Electrogeneration of Oxi-dized Corrole Dimers. Electrochemistry of (OEC) M Where M = Mn, Co, Ni, or Cu and OEC is the Trianion of 2, 3, 7, 8, 12, 13, 17, 18-Octaethylcorrole. J. Am. Chem. Soc. 1998. V. 120. P. 11986–11993.

Kahn O. Molecular Magnetism. VCH Publishers. 1993.

Thomas K.E., Alemayehu A.B., Conradie J., Beavers C.M., Ghosh A. The Structural Chemistry of Metallocor-roles: Combined X-ray Crystallography and Quantum Chem-istry Studies Afford Unique Insights. Acc. Chem. Res. 2012. V. 45. P. 1203–1214.

Michl J. Electronic structure of aromatic π-electron systems as reflected in their MCD spectra. Pure. Appl. Chem. 1980. V. 52. P. 1549–1563.

Michl J. Magnetic Circular Dichroism of Aromatic Mole-cules. Tetrahedron. 1984. V. 40. P. 3845–3934.

Mugarza A., Krull C., Robles R., Stepanow S., Ceballos G., Gambardella P. Spin Coupling and Relaxation Inside Molecule–Metal Contacts. Nat. Commun. 2011. V. 2. P. 490. DOI: 10.1038/ncomms1497.

Fukuda T., Homma S., Kobayashi N. Deformed Phthalo-cyanines: Synthesis and Characterization of Zinc Phthalocya-nines Bearing Phenyl Substituents at the 1-, 4-, 8-, 11-, 15-, 18-, 22-, and/or 25-Positions. Chem. Eur. J. 2005. V. 11. P. 5205-5216.

Kobayashi N., Fukuda T., Ueno K., Ogino H. Extremely Non-Planar Phthalocyanines with Saddle or Helical Confor-mation: Synthesis and Structural Characterizations. J. Am. Chem. Soc. 2001. V. 123. P. 10740-10741.

Fukuda T., Kobayashi N. A Colormap Analysis Method for Visual Presentation of the Skeletal Deformations of Phthalo-cyanine Derivatives. J. Porph. Phthal. 2004. V. 8. P. 1251-1257.

Sugimori T., Torikata M., Nojima J., Tominaka S., Tobi-kawa K., Handa M., Kasuga K. Preparation and properties of octa-substituted phthalocyanines peripherally substituted with phenyl derivatives. Inorg. Chem. Commun. 2002. V. 5. P. 1031-1033.

Konami H., Hatano H. Synthesis and Spectroscopic Proper-ties of Zn(II) Mono-2-(t-butyl)phthalocyanine. Chem. Lett. 1988. P. 1359-1362.

To confirm the “additivity”, we have synthesized a series of para-substituted a-octaphenyl Pcs, that is, αααα, αααβ, αβαβ (opp), ααββ (adj), and ββββ, where a denotes 3,6-diphenylphthalonitrile units and b denotes 3,6-bis(4-methoxyphenyl)-4,5-dicyanobenzene units. The ligand defor-mations are expected to be almost identical from complex to complex on the basis of the molecular structures, and they show reasonable additivities of the Q-band energies with re-spect to the number of methoxy groups. In particular, the op-posite and adjacent isomers show practically identical Q-band energies (i.e., 800 and 801 nm for metal-free αβαβ and ααββ isomers, respectively). Fukuda T., Doctoral Thesis, Tohoku University, 2004.

Fukuda T., Homma S., Kobayashi N. A Highly Deformed Iron(II) Low-Spin Phthalocyanine Which Shows Two MLCT Transitions beyond the Q-Band. Chem. Commun. 2003. P. 1574-1575.

Edwards L., Gouterman M. Porphyrins: XV. Vapor Ab-sorption Spectra and Stability: Phthalocyanines. J. Mol. Spectr. 1970. V. 33. P. 292-310.

Kobayashi N., Fukuda T. Mono-Aromatic Ring-Fused versus Adjacently Di-Aromatic Ring-Fused Tetraazaporphy-rins: Regioselective Synthesis and Their Spectroscopic and Electrochemical Properties. J. Am. Chem. Soc. 2002. V. 124. P. 8021-8034.

Kobayashi N., Miwa H., Nemykin V.N. Adjacent versus Opposite Type Di-Aromatic Ring-Fused Phthalocyanine De-rivatives: Synthesis, Spectroscopy, Electrochemistry, and Mo-lecular Orbital Calculations. J. Am. Chem. Soc. 2002. V. 124. P. 8007-8020.

Fukuda T., Makarova E.A., Luk’yanets E.A., Kobayashi N. Synthesis and Spectroscopic and Electrochemical Studies of Novel Benzo- or 2,3-Naphtho-Fused Tetraaza-chlorins, -bacteriochlorins, and -isobacteriochlorins. Chem. Eur. J. 2004. V. 10. P. 117-133.

Lever A.B.P., Milaeva E.R., Speier G. The Redox Chemis-try of Metallophthalocyanines in Solution. In “Phthalocya-nines – Properties and Applications”. Ed. by C.C. Leznoff, A.B.P. Lever. V. III. Chap. 1. New York: VCH. 1993.

Shimizu S., Hua Zhu H., Kobayashi N. Azaphenalene Phthalocyanines: Phthalocyanine Analogues with Six- Mem-bered-Ring Units Instead of Five-Membered-Ring Units. Chem. Eur. J. 2010. V. 16. P. 11151-11159.

Rodoriguez-Morgade M., De La Torre G., Torres T. Design and Synthe-sis of Low-Symmetry Phthalocuyanines and Related Systems. In “The Por-phyrin Handbook”. V. 15. Ed. by K.M. Kadish, K.M. Smith, R. Guilard. San Diego: Academic Press. 2003. pp. 125–160.

Oliver S.W., Smith T.D. Oligomeric Cyclization of Dinitriles in the Synthesis of Phthalocyanines and Related Compounds: the role of the Alkoxide Anion. J. Chem. Soc. Perkin Trans. 1987. V. 2. P.1579-1582.

Scheidt W.R. Systematics of the Stereochemistry of Porphy-rins and Metalloporphyrins. in “The Porphyrin Handbook”. V. 3. Ed. by K.M. Kadish, K.M. Smith, R. Guilard. San Die-go: Academic Press. 2000. pp. 49–112.

Kobayashi N., Nakajima S., Ogata H., Fukuda T. Synthe-sis, Spectroscopy, and Electrochemistry of Tetra-tert-Butylated Tetraazaporphyrins, Phthalocyanines, Naphthalocy-anines, and Anthracocyanines, together with Molecular Or-bital Calculations. Chem. Eur. J. 2004. V. 10. P. 6294-6312.

Honda T., Kojima T., Kobayashi N., Fukuzumi S. Crystal Structures and Electronic Properties of Saddle-Distorted and Protonated Phthalocyanines. Angew. Chem. Int. Ed. 2011. V. 50. P. 2725-2728.

Ogunsipe A., Nyokong T. Effects of Substituents and Sol-vents on the Photochemical Properties of Zinc Phthalocyanine Complexes and Their Protonated Derivatives. J. Mol. Struct. 2004. V. 689. P. 89-97.

a) Kojima T., Honda T., Ohkubo K., Shiro M., Kusukawa T., Fukuda T., Kobayashi N., Fukuzumi S. A Discrete Supramolecular Conglomerate Composed of Two Saddle-Distorted Zinc(II)-Phthalocyanine Complexes and a Doubly Protonated Porphyrin with Saddle-Distortion Undergoing Efficient Photoinduced Electron Transfer. Angew. Chem. Int. Ed. 2008. V. 47. P. 6712-6716. b) Honda T., Kojima T., Fukuzumi S. Crystal Structures and Properties of a Monoprotonated Porphyrin. Chem. Commun. 2009. P. 4994-4996.

Stuzhin P.A., Khelevina O.G., Berezin B.D. Azaporphy-rins: Acid-Base Properties. In “Phthalocyanines-Properties and Applications”. Ed. by C.C. Leznoff, A.B.P. Lever. V. IV. Chap. 2 (pp. 19-77). New York, Weinheim, Cambridge: VCH. 1996.

Shimizu S., Zhu H., Kobayashi N. Azepiphthalocyanine—an Unprecedented Large Twist of a π-Conjugation System upon Core-Modification with a Seven-Membered Ring Unit. Chem. Commun. 2011. V. 47. P. 3072–3074.

Fukuda T., Kobayashi N. Hydrogenated Tetraazaporphyrins - Old but New Core-Modified Phthalocyanine Analogues. Dalton Trans. 2008. P. 4685-4704.

Furuyama T., Ogura Y., Yoza K., Kobayashi N. Supera-zaporphyrins: Meso-Pentaazapentaphyrins and One of Their Low-Symmetry Derivatives. Angew. Chem. Int. Ed. 2012. V. 51. P. 11110–11114.

a) Bloor J.E., Schlabitz J., Walden C.C. Organic Complex-es of Uranium: Part I. The Synthesis and Spectrum of Uranyl Phthalocyanine. Can. J. Chem. 1964. V. 42. P. 2201-2208;

b) Day V.W., Marks T.J., Wachter W.A. Large Metal Ion-Centered Template Reactions. Uranyl Complex of Cyclo-pentakis(2-iminoisoindoline). J. Am. Chem. Soc. 1975. V. 97. P. 4519-4527.

a) Takeuchi Y., Matsuda A., Kobayashi N. Synthesis and Characterization of meso-Triarylsubporphyrins. J. Am. Chem. Soc. 2007. V. 129. P. 8271-8281. b) Kobayashi N., Takeuchi Y., Matsuda A. meso-Aryl Subporphyrins. An-gew. Chem. Int. Ed. 2007. V. 46. P. 758-760.

Claessens, C. G., Torres, T. Subphthalocyanines: Singular Nonplanar Aromatic Compounds - Synthesis, Reactivity, and Physical Properties. Chem. Rev. 2002. V. 102. P. 835-854.

Inokuma Y., Kwan J. H., Ahn T. K., Yoon M. C., Kim D., Osuka A. Tribenzosubporphines: Synthesis and Charac-terization. Angew. Chem., Int. Ed. 2006. V. 45. P. 961-964.

Stork J.R., Brewer J.J., Fukuda T., Fitzgerald J.P., Yee G.T., Nazarenko A.Y., Kobayashi N., Durfee W.S. Chloro and Hydroxo Forms of a Boron(III) Subtriazaporphyrin Mac-rocycle. Inorg. Chem. 2006. V. 45. P. 6148-6151.

Scheidt W.R., Kasatner M.E., Hatano K. Stereochemistry of the toluene solvate of ,,,-tetraphenylporphinato-zinc(II). Inorg. Chem. 1978. V. 17. P. 706-710.

Senge M.O. Database of Tetrapyrrole Crystal Structure De-terminations. Ed. by K. M. Kadish, K. M. Smith, R. Guilard. San Diego: Academic Press. 2000. V. 10. P. 1-218.

Kadish K.M., Royal G., Gueletti L. Metalloporphyrins in Nonaqueous Media: Database of Redox Potentials. In “The Porphyrin Handbook”. Ed. by K. M. Kadish, K. M. Smith, R. Guilard. San Diego: Academic Press. 2000. V. 9. Chap. 59. P. 1-219.

Rao T.A., Maiya B.G. Spectroscopic, Redox and Emission Properties of 2-Nitro-Substituted Free Base- and Metallo-Tetra-Aryl Porphyrins. Polyhedron. 1994. V. 13. P. 1863-1873.

Ishii K., Kobayashi N., Matsuo T., Tanaka M., Sekiguchi A. Observation of the Predicted Negative Faraday A MCD Term in a Cyclobutadiene Dianion. J. Am. Chem. Soc. 2001. V. 123. P. 5356-5357.

Kobayashi N., Ishizaki T., Ishii K., Konami H. Synthesis, Spectroscopy, and Molecular Orbital Calculations of Subaza-porphyrins, Subphthalocyanines, Subnaphthalocyanines, and Compounds Derived Therefrom by Ring Expansion. J. Am. Chem. Soc. 1999. V. 121. P. 9096-9110.

Stork J.R., Brewer J.J., Fukuda T., Fitzgerald J.P., Yee G.T., Nazarenko A.Y., Kobayashi N., Durfee W.S. . Chlo-ro and Hydroxo Forms of a Boron(III) Subtriazaporphyrin Macrocycle. Inorg. Chem. 2006. V. 45. P. 6148-6151.

Stillman M.J., Nyokong T. Absorption and Magnetic Circu-lar Dichroism Spectral Properties of Phthalocyanines. Part 1: Complexes of the Dianion, Pc(-2). In “Phthalocyanines-Properties and Applications”. Ed. by C.C. Leznoff, A.B.P. Lever. Weinheim: VCH. 1989. Chap. 3. P. 133-289.

Vancoillie S., Hendrickx M., Holz T., Nguyen M. T., Pier-loot K., Ceulemans A., Mack J., Kobayashi N. Fourteen-Electron Ring Model and the Anomolous Magnetic Circular Dsichroism of meso-Triarylsubporphyrins. J. Phys. Chem. A. 2012. V. 116. P. 3960−3967.

Seybold P. G., Gouterman M. Porphyrins: XIII: Fluores-cence Spectra and Quantum Yields. J. Mol. Spectrosc. 1969. V. 31. P. 1-13.

Xue Z. L., Shen Z., Mack J., Kuzuhara D., Yamada H., Okujima T., Ono N., You X. Z, Kobayashi N. A Facile One-Pot Synthesis of meso-Aryl-Substituted [14]Triphyrin(2.1.1). J. Am. Chem. Soc. 2008. V. 130. P. 16478–16479.

Опубликован
2019-04-06
Как цитировать
Kobayashi, N. (2019). СПЕКТРОСКОПИЧЕСКИ И/ИЛИ СТРУКТУРНО ИНТРИГУЮЩИЕ ФТАЛОЦИАНИНЫ И РОДСТВЕННЫЕ СОЕДИНЕНИЯ. ЧАСТЬ 1. МОНОМЕРНЫЕ СИСТЕМЫ. ИЗВЕСТИЯ ВЫСШИХ УЧЕБНЫХ ЗАВЕДЕНИЙ. СЕРИЯ «ХИМИЯ И ХИМИЧЕСКАЯ ТЕХНОЛОГИЯ», 62(4), 4-46. https://doi.org/10.6060/ivkkt.20196206.5913_1
Раздел
Обзорные статьи