258
S. Matsumoto and J. Hwang
Acknowledgements The authors thank Ms. Sayumi Hatano and Ms. Yuko Kishi for the CSD
search. This work was financially supported by the Center for Gender Equality and Diversity at
Yokohama National University.
References
Akune Y (2017) Study on the occurrence of polymorphs and the optical properties in a series of
benzylated diaminodicyanopyrazine dyes. PhD thesis, Yokohama National University
Akune Y, Gontani H, Hirosawa R, Koseki A, Matsumoto S (2015) The effects of molecular flexibility
and substituents on conformational polymorphism in a series of 2,5-diamino-3,6-dicyanopyrazine
dyes with highly flexible groups. CrystEngComm 17:5789–5800
Akune Y, Hirosawa R, Takahashi H, Shiro M, Matsumoto S (2016) Role of flexible bulky groups
and weak interactions involving halogens in the vapoluminescence of a metal-free dye. RSC Adv
6:74506–74509
Akune Y, Hirosawa R, Endo N, Hatano S, Hosokai T, Sato H, Matsumoto S (2017a) Tuning of fluorescence efficiency via local modification of the crystal structure by benzyl groups in polymorphs
of a pyrazine dye. CrystEngComm 19:1947–1952
Akune Y, Hirosawa R, Koseki A, Matsumoto S (2017b) Role of halogen substituents in a series
of polymorphic 2,5-diamino-3,6-dicyanopyrazine derivatives with highly flexible groups. Z
Kristallogr Cryst Mater 232:395–405
Ameri T, Dennler G, Lungenschmied C, Brabec CJ (2009) Organic tandem solar cells: a review.
Energy Environ Sci 2:347–363
Ashida M, Uyeda N, Suito E (1966) Unit cell metastable-form constants of various phthalocyanines.
Bull Chem Soc Jpn 39:2616–2624
Bernstein J (2002) Polymorphism in molecular crystals. Oxford University Press, Oxford
Bernstein J, Davey RJ, Henck JO (1999) Concomitant polymorphs. Angew Chem Int Ed 38:3440–
3461
Bluhm T, Mayo J, Hamer G, Martin T (1992) The application of Rietveld analysis to crystal
structures of titanyl phthalocyanine. Proc SPIE Int Soc Opt Eng 1670:160–171
Brown CJ (1968) Crystal structure of β-copper phthalocyanine. J Chem Soc A 2488–2493
Calligaro DO, Fairhurst J, Hotten TM, Moore NA, Tupper DE (1997) The synthesis and biological
activity of some known and putative metabolites of the atypical antipsychotic agent olanzapine
(LY170053). Bioorg Med Chem Let 7:25–30
Chen S, Guzei IA, Yu L (2005) New polymorphs of ROY and new record for coexisting polymorphs
of solved structures. J Am Chem Soc 127:9881–9885
Chung H, Diao Y (2016) Polymorphism as an emerging design strategy for high performance
organic electronics. J Mater Chem C 4:3915–3933
Cruz-Cabeza AJ, Bernstein J (2014) Conformational polymorphs. Chem Rev 114:2170–2191
Dunitz JD, Bernstein J (1995) Disappearing polymorphs. Acc Chem Res 28:193–200
Dunitz JD, Gavezzotti A (2005) Toward a quantitative description of crystal packing in
terms of molecular pairs: application to the hexamorphic crystal system, 5-Methyl-2-[(2nitrophenyl)amino]-3-thiophenecarbonitrile. Cryst Growth Des 5:2180–2189
Engel MK (1996) Single-crystal and solid-state molecular structures of phthalocyanine complexes.
Rep Kawamura Inst Chem Res 11–54
Engel MK (2003) Single crystal structures of phthalocianine complexes and related macrocycles.
In: Kadish K, Guillard R, Smith KM (eds) Handbook of porphyrins and phthalocyanines, vol 20.
Elsevier Science
Erk P (2004) Experimental crystal structure determination. CSD Communication
Erk P, Hengelsberg H (2003) Phthalocyanine dyes and pigments. In: Kadish K, Guillard R, Smith
KM (eds) Handbook of porphyrins and phthalocyanines, vol 19. Elsevier Science, pp 105–149
S. Matsumoto and J. Hwang
Acknowledgements The authors thank Ms. Sayumi Hatano and Ms. Yuko Kishi for the CSD
search. This work was financially supported by the Center for Gender Equality and Diversity at
Yokohama National University.
References
Akune Y (2017) Study on the occurrence of polymorphs and the optical properties in a series of
benzylated diaminodicyanopyrazine dyes. PhD thesis, Yokohama National University
Akune Y, Gontani H, Hirosawa R, Koseki A, Matsumoto S (2015) The effects of molecular flexibility
and substituents on conformational polymorphism in a series of 2,5-diamino-3,6-dicyanopyrazine
dyes with highly flexible groups. CrystEngComm 17:5789–5800
Akune Y, Hirosawa R, Takahashi H, Shiro M, Matsumoto S (2016) Role of flexible bulky groups
and weak interactions involving halogens in the vapoluminescence of a metal-free dye. RSC Adv
6:74506–74509
Akune Y, Hirosawa R, Endo N, Hatano S, Hosokai T, Sato H, Matsumoto S (2017a) Tuning of fluorescence efficiency via local modification of the crystal structure by benzyl groups in polymorphs
of a pyrazine dye. CrystEngComm 19:1947–1952
Akune Y, Hirosawa R, Koseki A, Matsumoto S (2017b) Role of halogen substituents in a series
of polymorphic 2,5-diamino-3,6-dicyanopyrazine derivatives with highly flexible groups. Z
Kristallogr Cryst Mater 232:395–405
Ameri T, Dennler G, Lungenschmied C, Brabec CJ (2009) Organic tandem solar cells: a review.
Energy Environ Sci 2:347–363
Ashida M, Uyeda N, Suito E (1966) Unit cell metastable-form constants of various phthalocyanines.
Bull Chem Soc Jpn 39:2616–2624
Bernstein J (2002) Polymorphism in molecular crystals. Oxford University Press, Oxford
Bernstein J, Davey RJ, Henck JO (1999) Concomitant polymorphs. Angew Chem Int Ed 38:3440–
3461
Bluhm T, Mayo J, Hamer G, Martin T (1992) The application of Rietveld analysis to crystal
structures of titanyl phthalocyanine. Proc SPIE Int Soc Opt Eng 1670:160–171
Brown CJ (1968) Crystal structure of β-copper phthalocyanine. J Chem Soc A 2488–2493
Calligaro DO, Fairhurst J, Hotten TM, Moore NA, Tupper DE (1997) The synthesis and biological
activity of some known and putative metabolites of the atypical antipsychotic agent olanzapine
(LY170053). Bioorg Med Chem Let 7:25–30
Chen S, Guzei IA, Yu L (2005) New polymorphs of ROY and new record for coexisting polymorphs
of solved structures. J Am Chem Soc 127:9881–9885
Chung H, Diao Y (2016) Polymorphism as an emerging design strategy for high performance
organic electronics. J Mater Chem C 4:3915–3933
Cruz-Cabeza AJ, Bernstein J (2014) Conformational polymorphs. Chem Rev 114:2170–2191
Dunitz JD, Bernstein J (1995) Disappearing polymorphs. Acc Chem Res 28:193–200
Dunitz JD, Gavezzotti A (2005) Toward a quantitative description of crystal packing in
terms of molecular pairs: application to the hexamorphic crystal system, 5-Methyl-2-[(2nitrophenyl)amino]-3-thiophenecarbonitrile. Cryst Growth Des 5:2180–2189
Engel MK (1996) Single-crystal and solid-state molecular structures of phthalocyanine complexes.
Rep Kawamura Inst Chem Res 11–54
Engel MK (2003) Single crystal structures of phthalocianine complexes and related macrocycles.
In: Kadish K, Guillard R, Smith KM (eds) Handbook of porphyrins and phthalocyanines, vol 20.
Elsevier Science
Erk P (2004) Experimental crystal structure determination. CSD Communication
Erk P, Hengelsberg H (2003) Phthalocyanine dyes and pigments. In: Kadish K, Guillard R, Smith
KM (eds) Handbook of porphyrins and phthalocyanines, vol 19. Elsevier Science, pp 105–149