116
S. Shimizu
Heremans P, Martínez-Díaz MV, Torres T, Cheyns D (2015) Energy level tuning of non-fullerene
acceptors in organic solar cells. J Am Chem Soc 137:8991–8997
(a) Gouterman M (1959) Study of the effects of substitution on the absorption spectra of porphin.
J Chem Phys 30:1139–1161; (b) Gouterman M (1961) Spectra of porphyrins. J Mol Spectrosc
6:138–163
Kobayashi N, Muranaka A, Mack J (2012) Circular dichroism and magnetic circular dichroism
spectroscopy for organic chemists. Royal Society of Chemistry, UK
(a) Mack J, Stillman MJ, Kobayashi N (2007) Application of MCD spectroscopy to porphyrinoids.
Coord Chem Rev 251:429–453; (b) Mack J, Kobayashi N, Shen Z (2012) The effect of structural
modifications on the properties of porphyrinoids. In: Kadish KM, Smith KM, Guilard R (eds)
Handbook of Porphyrin Science, vol 23. World Scientific, Singapore
(a) Michl J (1978) Magnetic circular dichroism of cyclic π-electron systems. 1. Algebraic solution
of the perimeter model for the A and B terms of high-symmetry systems with a (4N + 2)-electron
[n]annulene perimeter. J Am Chem Soc 100:6801–6811; (b) Michl J (1984) Magnetic circular
dichroism of aromatic molecules. Tetrahedron 40:3845–3934
Sharman WM, van Lier JE (2003) Synthesis of phthalocyanine precursors. In: Kadish KM, Smith
KM, Guilard R (eds) The Porphyrin Handbook, vol 15. Academic Press, San Diego, pp 1–60
McKeown NB (2003) The synthesis of symmetrical phthalocyanines. In: Kadish KM, Smith KM,
Guilard R (eds) The Porphyrin Handbook, vol 15. Academic Press, San Diego, pp 61–160
Tomoda H, Saito S, Ogawa S, Shiraishi S (1980) Synthesis of phthalocyanines from phthalonitrile
with organic strong bases. Chem Lett 9:1277–1280
Brach PJ, Grammatica SJ, Ossanna OA, Weinberger L (1970) Improved synthesis of metal-free
phthalocyanines. J Heterocycl Chem 7:1403–1405
(a) Uosaki K, Ueda J (1992) Photoelectrochemical synthesis of phthalocyanine. J Chem Soc, Perkin
Trans 2:1331–1333; (b) Yang CH, Lin SF, Chen HL, Chang CT (1980) Electrosynthesis of the
metal phthalocyanine complexes. Inorg Chem 19:3541–3543; (c) Petit MA, Plichon V, Belkacemi
H (1989). Nouv J Chim 13:459; (d) Petit MA, Thami T, Sirlin S, Lelievre D (1991). Nouv J Chim
15:71
Hall TH, Greenberg S, McArthur CR, Khouw B, Leznoff CC (1982) Nouv J Chim 6:653
Musluoglu E, Gürek A, Ahsen V, Gül A, Bekaroˇ glu ö, (1992) Unsymmetrical phthalocyanines with
a single macrocyclic substituent. Chem Ber 125:2337–2339
Claessens CG, González-Rodríguez D, del Rey B, Torres T, Mark G, Schuchmann H-P, von Sonntag
C, MacDonald JG, Nohr Ronald S (2003) Highly efficient synthesis of chloro- and phenoxysubstituted subphthalocyanines. Eur J Org Chem 2547–2551
Fukuda T, Kobayashi N (2010) UV-visible absorption sepctrscopic properties of phthalocyanines
and related macrocycles. In: Kadish KM, Smith KM, Guilard R (eds) Handbook of porphyrin
science, vol 9. World Scientific, Singapore
Simpson WT (1949) On the theory of the π-electron system in porphines. J Chem Phys 17:1218–
1221
Longuet-Higgins HC, Rector CW, Platt JR (1950) Molecular orbital calculations on porphine and
tetrahydroporphine. J Chem Phys 18:1174–1181
Mack J, Stillman MJ (2001) Assignment of the optical spectra of metal phthalocyanines through
spectral band deconvolution analysis and zindo calculations. Coord Chem Rev 219–221:993–
1032
Mack J, Stillman MJ (1995) Band deconvolution analysis of the absorption and magnetic circular
dichroism spectral data of ZnPc(-2) recorded at cryogenic temperatures. J Phys Chem 99:7935–
7945
Ledson DL, Twigg MV (1975) Acid-base behaviour of phthalocyanine. Inorg Chim Acta 13:43–46
Mack J, Kobayashi N (2011) Low symmetry phthalocyanines and their analogues. Chem Rev
111:281–321
Kobayashi N, Nakajima S-i, Ogata H, Fukuda T (2004) Synthesis, spectroscopy, and electrochemistry of tetra-tert-butylated tetraazaporphyrins, phthalocyanines, naphthalocyanines, and
anthracocyanines, together with molecular orbital calculations. Chem –Eur J 10:6294–6312
S. Shimizu
Heremans P, Martínez-Díaz MV, Torres T, Cheyns D (2015) Energy level tuning of non-fullerene
acceptors in organic solar cells. J Am Chem Soc 137:8991–8997
(a) Gouterman M (1959) Study of the effects of substitution on the absorption spectra of porphin.
J Chem Phys 30:1139–1161; (b) Gouterman M (1961) Spectra of porphyrins. J Mol Spectrosc
6:138–163
Kobayashi N, Muranaka A, Mack J (2012) Circular dichroism and magnetic circular dichroism
spectroscopy for organic chemists. Royal Society of Chemistry, UK
(a) Mack J, Stillman MJ, Kobayashi N (2007) Application of MCD spectroscopy to porphyrinoids.
Coord Chem Rev 251:429–453; (b) Mack J, Kobayashi N, Shen Z (2012) The effect of structural
modifications on the properties of porphyrinoids. In: Kadish KM, Smith KM, Guilard R (eds)
Handbook of Porphyrin Science, vol 23. World Scientific, Singapore
(a) Michl J (1978) Magnetic circular dichroism of cyclic π-electron systems. 1. Algebraic solution
of the perimeter model for the A and B terms of high-symmetry systems with a (4N + 2)-electron
[n]annulene perimeter. J Am Chem Soc 100:6801–6811; (b) Michl J (1984) Magnetic circular
dichroism of aromatic molecules. Tetrahedron 40:3845–3934
Sharman WM, van Lier JE (2003) Synthesis of phthalocyanine precursors. In: Kadish KM, Smith
KM, Guilard R (eds) The Porphyrin Handbook, vol 15. Academic Press, San Diego, pp 1–60
McKeown NB (2003) The synthesis of symmetrical phthalocyanines. In: Kadish KM, Smith KM,
Guilard R (eds) The Porphyrin Handbook, vol 15. Academic Press, San Diego, pp 61–160
Tomoda H, Saito S, Ogawa S, Shiraishi S (1980) Synthesis of phthalocyanines from phthalonitrile
with organic strong bases. Chem Lett 9:1277–1280
Brach PJ, Grammatica SJ, Ossanna OA, Weinberger L (1970) Improved synthesis of metal-free
phthalocyanines. J Heterocycl Chem 7:1403–1405
(a) Uosaki K, Ueda J (1992) Photoelectrochemical synthesis of phthalocyanine. J Chem Soc, Perkin
Trans 2:1331–1333; (b) Yang CH, Lin SF, Chen HL, Chang CT (1980) Electrosynthesis of the
metal phthalocyanine complexes. Inorg Chem 19:3541–3543; (c) Petit MA, Plichon V, Belkacemi
H (1989). Nouv J Chim 13:459; (d) Petit MA, Thami T, Sirlin S, Lelievre D (1991). Nouv J Chim
15:71
Hall TH, Greenberg S, McArthur CR, Khouw B, Leznoff CC (1982) Nouv J Chim 6:653
Musluoglu E, Gürek A, Ahsen V, Gül A, Bekaroˇ glu ö, (1992) Unsymmetrical phthalocyanines with
a single macrocyclic substituent. Chem Ber 125:2337–2339
Claessens CG, González-Rodríguez D, del Rey B, Torres T, Mark G, Schuchmann H-P, von Sonntag
C, MacDonald JG, Nohr Ronald S (2003) Highly efficient synthesis of chloro- and phenoxysubstituted subphthalocyanines. Eur J Org Chem 2547–2551
Fukuda T, Kobayashi N (2010) UV-visible absorption sepctrscopic properties of phthalocyanines
and related macrocycles. In: Kadish KM, Smith KM, Guilard R (eds) Handbook of porphyrin
science, vol 9. World Scientific, Singapore
Simpson WT (1949) On the theory of the π-electron system in porphines. J Chem Phys 17:1218–
1221
Longuet-Higgins HC, Rector CW, Platt JR (1950) Molecular orbital calculations on porphine and
tetrahydroporphine. J Chem Phys 18:1174–1181
Mack J, Stillman MJ (2001) Assignment of the optical spectra of metal phthalocyanines through
spectral band deconvolution analysis and zindo calculations. Coord Chem Rev 219–221:993–
1032
Mack J, Stillman MJ (1995) Band deconvolution analysis of the absorption and magnetic circular
dichroism spectral data of ZnPc(-2) recorded at cryogenic temperatures. J Phys Chem 99:7935–
7945
Ledson DL, Twigg MV (1975) Acid-base behaviour of phthalocyanine. Inorg Chim Acta 13:43–46
Mack J, Kobayashi N (2011) Low symmetry phthalocyanines and their analogues. Chem Rev
111:281–321
Kobayashi N, Nakajima S-i, Ogata H, Fukuda T (2004) Synthesis, spectroscopy, and electrochemistry of tetra-tert-butylated tetraazaporphyrins, phthalocyanines, naphthalocyanines, and
anthracocyanines, together with molecular orbital calculations. Chem –Eur J 10:6294–6312