4 Phthalocyanine and Related Analogues
117
(a) Kaito A, Nozawa T, Yamamoto T, Hatano M, Orii Y (1977) LCAO MO Scf π-Electron
calculations on the magnetic circular dichroism of porphin, protoporphyrin, and porphyrin.
Chem Phys Lett 52:154–160; (b) Tajiri A, Winkler J (1983) Magnetic circular-dichroism and
molecular-orbital studies on condensed thiadiazoles. Z Naturforsch A 38:1263–1269
Miwa H, Ishii K, Kobayashi N (2004) Electronic structures of zinc and palladium tetraazaporphyrin
derivatives controlled by fused benzo rings. Chem –Eur J 10:4422–4435
Fukuda T, Makarova EA, Luk’yanets EA, Kobayashi N (2004) Synthesis and spectroscopic and
electrochemical studies of novel benzo- or 2,3-naphtho-fused tetraazachlorins, bacteriochlorins,
and isobacteriochlorins. Chem –Eur J 10:117–133
Shimizu S, Haseba Y, Yamazaki M, Kumazawa G, Kobayashi N (2014) Control of chromophore
symmetry by positional isomerism of peripheral substituents. Chem –Eur J 20:4822–4828
Liang X, Shimizu S, Kobayashi N (2014) Sizeable red-shift of absorption and fluorescence of
subporphyrazine induced by peripheral push and pull substitution. Chem Commun 50:13781–
13784
Shimizu S, Miura A, Khene S, Nyokong T, Kobayashi N (2011) Chiral 1,2-subnaphthalocyanines.
J Am Chem Soc 133:17322–17328
(a) Furuyama T, Kobayashi N (2017) Azaporphyrin phosphorus(v) complexes: synthesis, structure,
and modification of optical properties. Phys Chem Chem Phys 19:15596–15612; (b) Kobayashi N,
Furuyama T, Satoh K (2011) Rationally designed phthalocyanines having their main absorption
band beyond 1000 nm. J Am Chem Soc 133:19642–19645
Tanaka T, Osuka A (2017) Chemistry of meso-aryl-substituted expanded porphyrins: aromaticity
and molecular twist. Chem Rev 117:2584–2640
Bloor JE, Schlabitz J, Walden CC, Demerdache A (1964) Organic complexes of uranium: Part I.
The synthesis and spectrum of uranyl phthalocyanine. Can J Chem 42:2201–2208
(a) Day VW, Marks TJ, Wachter WA (1975) Large metal ion-centered template reactions: uranyl
complex of cyclopentakis(2-iminoisoindoline). J Am Chem Soc 97:4519–4527; (b) Cuellar EA,
Marks TJ (1981) Synthesis and characterization of metallo and metal-free octaalkylphthalocyanines and uranyl decaalkylsuperphthalocyaninates. Inorg Chem 20:3766–3770; (c) Marks TJ,
Stojakovic DR (1978) Large metal ion-centered template reactions. chemical and spectral studies
of the “Superphthalocyanine” Dioxocyclopentakis(1-iminoisoindolinato)uranium(VI) and its
derivatives. J Am Chem Soc 100:1695–1705
Furuyama T, Ogura Y, Yoza K, Kobayashi N (2012) Superazaporphyrins: mesopentaazapentaphyrins and one of their low-symmetry derivatives. Angew Chem Int Ed
51:11110–11114
Rodríguez-Morgade MS, Cabezón B, Esperanza S, Torres T (2001) Expanded phthalocyanine
analogues: synthesis and characterization of new triazole-derived annulenes containing six
heterocyclic subunits. Chem –Eur J 7:2407–2413
Kobayashi N, Inagaki S, Nemykin VN, Nonomura T (2001) A novel hemiporphyrazine comprising
three isoindolediimine and three thiadiazole units. Angew Chem Int Ed 40:2710–2712
(a) Islyaikin MK, Danilova EA, Yagodarova LD, Rodríguez-Morgade MS, Torres T (2001)
Thiadiazole-derived expanded heteroazaporphyrinoids. Org Lett 3:2153–2156; (b) Trukhina ON,
Rodríguez-Morgade MS, Wolfrum S, Caballero E, Snejko N, Danilova EA, Gutierrez-Puebla E,
Islyaikin MK, Guldi DM, Torres T (2010) Scrutinizing the chemical nature and photophysics of
an expanded hemiporphyrazine: the special case of [30]Trithia-2,3,5,10,12,13,15,20,22,23,25,30dodecaazahexaphyrin. J Am Chem Soc 132:12991–12999
Furuyama T, Sato T, Kobayashi N (2015) A bottom-up synthesis of antiaromatic expanded phthalocyanines: pentabenzotriazasmaragdyrins, i.e. norcorroles of superphthalocyanines. J Am Chem
Soc 137:13788–13791
Pareek Y, Ravikanth M, Chandrashekar TK (2012) Smaragdyrins: emeralds of expanded porphyrin
family. Acc Chem Res 45:1801–1816
(a) Howeler UW, Downing J, Fleischhauer J, Michl J (1998) MCD of non-aromatic cyclic π-electron
systems. Part 1. The perimeter model for antiaromatic 4N-electron [n]annulene biradicals 1. J
Chem Soc, Perkin Trans 2:1101–1118; (b) Fleischhauer J, Höweler U, Michl J (2000) MCD
117
(a) Kaito A, Nozawa T, Yamamoto T, Hatano M, Orii Y (1977) LCAO MO Scf π-Electron
calculations on the magnetic circular dichroism of porphin, protoporphyrin, and porphyrin.
Chem Phys Lett 52:154–160; (b) Tajiri A, Winkler J (1983) Magnetic circular-dichroism and
molecular-orbital studies on condensed thiadiazoles. Z Naturforsch A 38:1263–1269
Miwa H, Ishii K, Kobayashi N (2004) Electronic structures of zinc and palladium tetraazaporphyrin
derivatives controlled by fused benzo rings. Chem –Eur J 10:4422–4435
Fukuda T, Makarova EA, Luk’yanets EA, Kobayashi N (2004) Synthesis and spectroscopic and
electrochemical studies of novel benzo- or 2,3-naphtho-fused tetraazachlorins, bacteriochlorins,
and isobacteriochlorins. Chem –Eur J 10:117–133
Shimizu S, Haseba Y, Yamazaki M, Kumazawa G, Kobayashi N (2014) Control of chromophore
symmetry by positional isomerism of peripheral substituents. Chem –Eur J 20:4822–4828
Liang X, Shimizu S, Kobayashi N (2014) Sizeable red-shift of absorption and fluorescence of
subporphyrazine induced by peripheral push and pull substitution. Chem Commun 50:13781–
13784
Shimizu S, Miura A, Khene S, Nyokong T, Kobayashi N (2011) Chiral 1,2-subnaphthalocyanines.
J Am Chem Soc 133:17322–17328
(a) Furuyama T, Kobayashi N (2017) Azaporphyrin phosphorus(v) complexes: synthesis, structure,
and modification of optical properties. Phys Chem Chem Phys 19:15596–15612; (b) Kobayashi N,
Furuyama T, Satoh K (2011) Rationally designed phthalocyanines having their main absorption
band beyond 1000 nm. J Am Chem Soc 133:19642–19645
Tanaka T, Osuka A (2017) Chemistry of meso-aryl-substituted expanded porphyrins: aromaticity
and molecular twist. Chem Rev 117:2584–2640
Bloor JE, Schlabitz J, Walden CC, Demerdache A (1964) Organic complexes of uranium: Part I.
The synthesis and spectrum of uranyl phthalocyanine. Can J Chem 42:2201–2208
(a) Day VW, Marks TJ, Wachter WA (1975) Large metal ion-centered template reactions: uranyl
complex of cyclopentakis(2-iminoisoindoline). J Am Chem Soc 97:4519–4527; (b) Cuellar EA,
Marks TJ (1981) Synthesis and characterization of metallo and metal-free octaalkylphthalocyanines and uranyl decaalkylsuperphthalocyaninates. Inorg Chem 20:3766–3770; (c) Marks TJ,
Stojakovic DR (1978) Large metal ion-centered template reactions. chemical and spectral studies
of the “Superphthalocyanine” Dioxocyclopentakis(1-iminoisoindolinato)uranium(VI) and its
derivatives. J Am Chem Soc 100:1695–1705
Furuyama T, Ogura Y, Yoza K, Kobayashi N (2012) Superazaporphyrins: mesopentaazapentaphyrins and one of their low-symmetry derivatives. Angew Chem Int Ed
51:11110–11114
Rodríguez-Morgade MS, Cabezón B, Esperanza S, Torres T (2001) Expanded phthalocyanine
analogues: synthesis and characterization of new triazole-derived annulenes containing six
heterocyclic subunits. Chem –Eur J 7:2407–2413
Kobayashi N, Inagaki S, Nemykin VN, Nonomura T (2001) A novel hemiporphyrazine comprising
three isoindolediimine and three thiadiazole units. Angew Chem Int Ed 40:2710–2712
(a) Islyaikin MK, Danilova EA, Yagodarova LD, Rodríguez-Morgade MS, Torres T (2001)
Thiadiazole-derived expanded heteroazaporphyrinoids. Org Lett 3:2153–2156; (b) Trukhina ON,
Rodríguez-Morgade MS, Wolfrum S, Caballero E, Snejko N, Danilova EA, Gutierrez-Puebla E,
Islyaikin MK, Guldi DM, Torres T (2010) Scrutinizing the chemical nature and photophysics of
an expanded hemiporphyrazine: the special case of [30]Trithia-2,3,5,10,12,13,15,20,22,23,25,30dodecaazahexaphyrin. J Am Chem Soc 132:12991–12999
Furuyama T, Sato T, Kobayashi N (2015) A bottom-up synthesis of antiaromatic expanded phthalocyanines: pentabenzotriazasmaragdyrins, i.e. norcorroles of superphthalocyanines. J Am Chem
Soc 137:13788–13791
Pareek Y, Ravikanth M, Chandrashekar TK (2012) Smaragdyrins: emeralds of expanded porphyrin
family. Acc Chem Res 45:1801–1816
(a) Howeler UW, Downing J, Fleischhauer J, Michl J (1998) MCD of non-aromatic cyclic π-electron
systems. Part 1. The perimeter model for antiaromatic 4N-electron [n]annulene biradicals 1. J
Chem Soc, Perkin Trans 2:1101–1118; (b) Fleischhauer J, Höweler U, Michl J (2000) MCD