4 Phthalocyanine and Related Analogues
115
Kadish KM, Smith KM, Guilard R (eds) (2003) The porphyrin handbook vol 15–20. Academic
Press, San Diego
Leznoff CC, Lever ABP (eds) (1989–1996) Phthalocyanines: properties and applications vol 1–4.
Wiley-VCH, New York
McKeown NB (1998) Phthalocyanine materials: synthesis. Cambridge University Press,
Cambridge, Structure and Function
Kobayashi N, Fukuda T (2006) Functional Dyes. In: Kim S (ed) Elsevier, Oxford
Meller A, Ossko A (1972) Triisindolo[1,2,3-Cd-1’,2’,3’-Gh-1”,2”,3”-Kl][2,3a,5,6a,8,9a,9b]-HenaAzaboraphenalene. Monatsh Chem 103:150–155
(a) Sessler JL, Gross Z, Furuta H (2017) Introduction: Expanded, Contracted, and Isomeric
Porphyrins. Chem Rev 117:2201–2202; (b) Sessler JL, Weghorn SJ (1997) Expanded, contracted,
and isomeric porphyrins. Pergamon Press, New York
(a) Claessens CG, González-Rodríguez D, Rodríguez-Morgade MS, Medina A, Torres T (2014)
Subphthalocyanines, subporphyrazines, and subporphyrins: singular nonplanar aromatic systems.
Chem Rev 114:2192–2277; (b) Claessens CG, González-Rodríguez D, Torres T (2002)
Subphthalocyanines: singular nonplanar aromatic compounds-synthesis, reactivity, and physical
properties. Chem Rev 102:835–853
(a) Shimizu S, Nakano S, Hosoya T, Kobayashi N (2011) Pyrene-fused subphthalocyanine. Chem
Commun 47:316–318; (b) Nakano S, Kage Y, Furuta H, Kobayashi N, Shimizu S (2016) Pyrenebridged boron subphthalocyanine dimers: combination of planar and bowl-shaped π-conjugated
systems for creating uniquely curved π-conjugated systems. Chem –Eur J 22:7706–7710
(a) Sánchez-Molina I, Claessens CG, Grimm B, Guldi DM, Torres T (2013) Trapping fullerenes with
jellyfish-like subphthalocyanines. Chem Sci 4:1338–1344; (b) Sánchez-Molina I, Grimm B, Krick
Calderon RM, Claessens CG, Guldi DM, Torres T (2013) Self-assembly, host–guest chemistry,
and photophysical properties of subphthalocyanine-based metallosupramolecular capsules. J Am
Chem Soc 135:10503–10511
Konarev DV, Troyanov SI, Lyubovskaya RN (2015) Coordination complex of boron subphthalocyanine (BSubPc) with fluorenone pinacolate: effective π–π interaction of concave BSubPc
macrocycle with fullerene C 60 . CrystEngComm 17:3923–3926
Rhoda HM, Kayser MP, Wang Y, Nazarenko AY, Belosludov RV, Kiprof P, Blank DA, Nemykin VN
(2016) Tuning up an electronic structure of the subphthalocyanine derivatives toward electrontransfer process in noncovalent complexes with C 60 and C 70 fullerenes: experimental and
theoretical studies. Inorg Chem 55:9549–9563
(a) Sastre A, Torres T, Díaz-García MA, Agulló-López F, Dhenaut C, Brasselet S, Ledoux I, Zyss
J (1996) Subphthalocyanines: novel targets for remarkable second-order optical nonlinearities.
J Am Chem Soc 118:2746–2747; (b) Martín G, Rojo G, Agulló-López F, Ferro VR, García
de la Vega JM, Martínez-Díaz MV, Torres T, Ledoux I, Zyss J (2002) Subphthalocyanines and
subnaphthalocyanines: nonlinear quasi-planar octupolar systems with permanent polarity. J Phys
Chem B 106:13139–13145
Renshaw CK, Xu X, Forrest SR (2010) A monolithically integrated organic photodetector and thin
film transistor. Org Electron 11:175–178
(a) Morse GE, Castrucci JS, Helander MG, Lu Z-H, Bender TP (2011) Phthalimidoboronsubphthalocyanines: new derivatives of boronsubphthalocyanine with bipolar electrochemistry and functionality in OLEDs. ACS Appl Mater Interfaces 3:3538–3544; (b) Helander MG,
Morse GE, Qiu J, Castrucci JS, Bender TP, Lu Z-H (2010) Pentafluorophenoxy boron subphthalocyanine as a fluorescent dopant emitter in organic light emitting diodes. ACS Appl Mater
Interfaces 2:3147–3152
Mutolo KL, Mayo EI, Rand BP, Forrest SR, Thompson ME (2006) Enhanced open-circuit voltage
in subphthalocyanine/C 60 organic photovoltaic cells. J Am Chem Soc 128:8108–8109
(a) Duan C, Zango G, García-Iglesias M, Colberts FJM, Wienk MM, Martínez-Díaz MV, Janssen
RAJ, Torres T (2016) The role of the axial substituent in subphthalocyanine acceptors for bulkheterojunction solar cells. Angew Chem Int Ed 56:154–158; (b) Cnops K, Zango G, Genoe J,
115
Kadish KM, Smith KM, Guilard R (eds) (2003) The porphyrin handbook vol 15–20. Academic
Press, San Diego
Leznoff CC, Lever ABP (eds) (1989–1996) Phthalocyanines: properties and applications vol 1–4.
Wiley-VCH, New York
McKeown NB (1998) Phthalocyanine materials: synthesis. Cambridge University Press,
Cambridge, Structure and Function
Kobayashi N, Fukuda T (2006) Functional Dyes. In: Kim S (ed) Elsevier, Oxford
Meller A, Ossko A (1972) Triisindolo[1,2,3-Cd-1’,2’,3’-Gh-1”,2”,3”-Kl][2,3a,5,6a,8,9a,9b]-HenaAzaboraphenalene. Monatsh Chem 103:150–155
(a) Sessler JL, Gross Z, Furuta H (2017) Introduction: Expanded, Contracted, and Isomeric
Porphyrins. Chem Rev 117:2201–2202; (b) Sessler JL, Weghorn SJ (1997) Expanded, contracted,
and isomeric porphyrins. Pergamon Press, New York
(a) Claessens CG, González-Rodríguez D, Rodríguez-Morgade MS, Medina A, Torres T (2014)
Subphthalocyanines, subporphyrazines, and subporphyrins: singular nonplanar aromatic systems.
Chem Rev 114:2192–2277; (b) Claessens CG, González-Rodríguez D, Torres T (2002)
Subphthalocyanines: singular nonplanar aromatic compounds-synthesis, reactivity, and physical
properties. Chem Rev 102:835–853
(a) Shimizu S, Nakano S, Hosoya T, Kobayashi N (2011) Pyrene-fused subphthalocyanine. Chem
Commun 47:316–318; (b) Nakano S, Kage Y, Furuta H, Kobayashi N, Shimizu S (2016) Pyrenebridged boron subphthalocyanine dimers: combination of planar and bowl-shaped π-conjugated
systems for creating uniquely curved π-conjugated systems. Chem –Eur J 22:7706–7710
(a) Sánchez-Molina I, Claessens CG, Grimm B, Guldi DM, Torres T (2013) Trapping fullerenes with
jellyfish-like subphthalocyanines. Chem Sci 4:1338–1344; (b) Sánchez-Molina I, Grimm B, Krick
Calderon RM, Claessens CG, Guldi DM, Torres T (2013) Self-assembly, host–guest chemistry,
and photophysical properties of subphthalocyanine-based metallosupramolecular capsules. J Am
Chem Soc 135:10503–10511
Konarev DV, Troyanov SI, Lyubovskaya RN (2015) Coordination complex of boron subphthalocyanine (BSubPc) with fluorenone pinacolate: effective π–π interaction of concave BSubPc
macrocycle with fullerene C 60 . CrystEngComm 17:3923–3926
Rhoda HM, Kayser MP, Wang Y, Nazarenko AY, Belosludov RV, Kiprof P, Blank DA, Nemykin VN
(2016) Tuning up an electronic structure of the subphthalocyanine derivatives toward electrontransfer process in noncovalent complexes with C 60 and C 70 fullerenes: experimental and
theoretical studies. Inorg Chem 55:9549–9563
(a) Sastre A, Torres T, Díaz-García MA, Agulló-López F, Dhenaut C, Brasselet S, Ledoux I, Zyss
J (1996) Subphthalocyanines: novel targets for remarkable second-order optical nonlinearities.
J Am Chem Soc 118:2746–2747; (b) Martín G, Rojo G, Agulló-López F, Ferro VR, García
de la Vega JM, Martínez-Díaz MV, Torres T, Ledoux I, Zyss J (2002) Subphthalocyanines and
subnaphthalocyanines: nonlinear quasi-planar octupolar systems with permanent polarity. J Phys
Chem B 106:13139–13145
Renshaw CK, Xu X, Forrest SR (2010) A monolithically integrated organic photodetector and thin
film transistor. Org Electron 11:175–178
(a) Morse GE, Castrucci JS, Helander MG, Lu Z-H, Bender TP (2011) Phthalimidoboronsubphthalocyanines: new derivatives of boronsubphthalocyanine with bipolar electrochemistry and functionality in OLEDs. ACS Appl Mater Interfaces 3:3538–3544; (b) Helander MG,
Morse GE, Qiu J, Castrucci JS, Bender TP, Lu Z-H (2010) Pentafluorophenoxy boron subphthalocyanine as a fluorescent dopant emitter in organic light emitting diodes. ACS Appl Mater
Interfaces 2:3147–3152
Mutolo KL, Mayo EI, Rand BP, Forrest SR, Thompson ME (2006) Enhanced open-circuit voltage
in subphthalocyanine/C 60 organic photovoltaic cells. J Am Chem Soc 128:8108–8109
(a) Duan C, Zango G, García-Iglesias M, Colberts FJM, Wienk MM, Martínez-Díaz MV, Janssen
RAJ, Torres T (2016) The role of the axial substituent in subphthalocyanine acceptors for bulkheterojunction solar cells. Angew Chem Int Ed 56:154–158; (b) Cnops K, Zango G, Genoe J,