Solid-state [2+2] photodimerization and photopolymerization of α,ω-diarylpolyene monomers: Effective utilization of noncovalent intermolecular interactions in crystals

Molecules

Volumn 16, Issue 1, 2011, Pages 119-148

  Sonoda, Yoriko ^a  

^a NATIONAL INSTITUTE OF ADVANCED INDUSTRIAL SCIENCE AND TECHNOLOGY AIST   (Japan)

Author keywords

2+2 Photocycloaddition; Cyclobutane; Hydrogen bond; Ring substituted diphenylhexatriene; Stacking arrangement

Indexed keywords

FLUORINE; POLYENE;

CHEMISTRY; CRYSTALLIZATION; CYCLIZATION; DIMERIZATION; HYDROGEN BOND; INFRARED SPECTROPHOTOMETRY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PHOTOCHEMISTRY; REVIEW;

CRYSTALLIZATION; CYCLIZATION; DIMERIZATION; FLUORINE; HYDROGEN BONDING; MAGNETIC RESONANCE SPECTROSCOPY; PHOTOCHEMISTRY; POLYENES; SPECTROPHOTOMETRY, INFRARED;

EID: 79251502987     PISSN: None     EISSN: 14203049     Source Type: Journal    
DOI: 10.3390/molecules16010119     Document Type: Review

References (172)

1. Schmidt, G. M. J. Photodimerization in the solid state. Pure Appl. Chem. 1971, 27, 647-678.
2. Cohen, M. D. The photochemistry of organic solids. Angew. Chem. Int. Ed. Engl. 1975, 14, 386-393.
3. Green, B. S.; Lahav, M.; Rabinovich, D. Asymmetric synthesis via reactions in chiral crystals. Acc. Chem. Res. 1979, 12, 191-197.
4. Gavezzotti, A.; Simonetta, M. Crystal chemistry in organic solids. Chem. Rev. 1982, 82, 1-13.
5. Ramamurthy, V. Organic photochemistry in organized media. Tetrahedron 1986, 42, 5753-5839.
6. Ramamurthy, V.; Venkatesan, K. Photochemical reactions of organic crystals. Chem. Rev. 1987, 87, 433-481.
7. Murthy, G. S.; Arjunan, P.; Venkatesan, K.; Ramamurthy, V. Consequences of lattice relaxability in solid state photodimerizations. Tetrahedron 1987, 43, 1225-1240.
8. Ohashi, Y. Dynamical structure analysis of crystalline-state racemization. Acc. Chem. Res. 1988, 21, 268-274.
9. Ramamurthy, V., Ed. Photochemistry in Organized and Constrained Media; VCH: New York, NY, USA, 1991.
10. Koshima, H.; Matsuura, T. Solid state photoreactions occurring at the interface between crystallites of two different organic compounds. J. Photochem. Photobiol. A Chem. 1996, 100, 85-91.
11. Ito, Y. Solid-state photoreactions in two-component crystals. Synthesis 1998, 1, 1-32.
12. Sonoda, Y. [2+2]-Photocycloadditions in the solid state. In CRC Handbook of Organic Photochemistry and Photobiology, 2nd ed.; Horspool, W., Lenci, F., Eds.; CRC Press: Boca Raton, FL, USA, 2004; Chapter 73.
13. Friščić, T.; MacGillivray, L. R. Single-crystal-to-single-crystal [2+2] photodimerizations: From discovery to design. Z. Kristallogr. 2005, 220, 351-363.
14. Toda, F. Solid state organic chemistry: Efficient reactions, remarkable yields, and stereoselectivity. Acc. Chem. Res. 1995, 28, 480-486.
15. Tanaka, K.; Toda, F. Solvent-free organic synthesis. Chem. Rev. 2000, 100, 1025-1074.
16. Toda, F. Thermal and photochemical reactions in the solid state. Top. Curr. Chem. 2005, 254, 1-40.
17. Kaupp, G. Waste-free synthesis and production all across chemistry with the benefit of selfassembled crystal packings. J. Phys. Org. Chem. 2008, 21, 630-643.
18. Maekawa, Y.; Lim, P.-J.; Saigo, K.; Hasegawa, M. Preparation of a crystalline linear high copolymer by topochemical photopolymerization of diolefin mixed crystals. Macromolecules 1991, 24, 5752-5755.
19. Braga, D.; Grepioni, F. Reactions between or within molecular crystals. Angew. Chem. Int. Ed. 2004, 43, 4002-4011.
20. Avendaño, C.; Briceño, A. Concomitant [2+2] cycloaddition solid state reactions from co-crystals self-assembled via mechanochemistry. CrystEngCommunity 2009, 11, 408-411.
21. Nagarathinam, M.; Vittal, J. J. Solid-state synthesis of coordination polymers for [2+2] photoreactions by grinding. Aust. J. Chem. 2010, 63, 589-595.
22. Peedikakkal, A. M. P.; Vittal, J. J. Solid-state photochemical behavior of a triple-stranded ladder coordination polymer. Inorg. Chem. 2010, 49, 10-12.
23. Cohen, M. D.; Schmidt, G. M. J. Topochemistry. Part I. A survey. J. Chem. Soc. 1964, 1996-2000.
24. Cohen, M. D.; Schmidt, G. M. J.; Sonntag, F. I. Topochemistry. Part II. The photochemistry of trans-cinnamic acids. J. Chem. Soc. 1964, 2000-2013.
25. Schmidt, G. M. J. Topochemistry. Part III. The crystal chemistry of some trans-cinnamic acids. J. Chem. Soc. 1964, 2014-2021.
26. Quina, F. H.; Whitten, D. G. Photochemical reactions in organized monolayer assemblies. 4. Photodimerization, photoisomerization, and excimer formation with surfactant olefins and dienes in monolayer assemblies, crystals, and micelles. J. Am. Chem. Soc. 1977, 99, 877-883.
27. Novak, K.; Enkelmann, V.; Wegner, G.; Wagener, K. B. Crystallographic study of a single crystal to single crystal photodimerization and its thermal reverse reaction. Angew. Chem. Int. Ed. Engl. 1993, 32, 1614-1616.
28. Kole, G. K.; Tan, G. K.; Vittal, J. J. Anion-controlled stereoselective synthesis of cyclobutane derivatives by solid-state [2+2] cycloaddition reaction of the salts of trans-3-(4-pyridyl) acrylic acid. Org. Lett. 2010, 12, 128-131.
29. Vedernikov, A. I.; Kuźmina, L. G.; Sazonov, S. K.; Lobova, N. A.; Loginov, P. S.; Churakov, A. V.; Strelenko, Y. A.; Howard, J. A. K.; Alfimov, M. V.; Gromov, S. P. Styryl dyes. Synthesis and study of the solid-state [2+2] autophotocycloaddition by NMR spectroscopy and X-ray diffraction. Russ. Chem. Bull. Int. Ed. 2007, 56, 1860-1883.
30. Kuz'mina, L. G.; Vedernikov, A. I.; Sazonov, S. K.; Lobova, N. A.; Loginov, P. S.; Howard, J. A. K.; Alfimov, M. V.; Gromov, S. P. Specific features of the crystal packing that enable styryl dyes of the pyridine series to undergo the solid-phase [2+2] photocycloaddition including the process with single crystal retention. Crystallogr. Rep. 2008, 53, 428-450.
31. Tulyakova, E. V.; Fedorova, O. A.; Fedorov, Y. V.; Anisimov, A. V. [2+2]-Photocycloaddition reaction of self-assembled crown-containing 2-styrylpyridinium perchlorate in a solid state. J. Photochem. Photobiol. A Chem. 2008, 200, 90-95.
32. Kuźmina, L. G.; Vedernikov, A. I.; Lobova, N. A.; Sazonov, S. K.; Basok, S. S.; Howard, J. A. K.; Gromov, S. P. Design of crystal packings of styrylheterocycles and [2+2] photocycloaddition reactions in their single crystals 6. Synthesis and crystal packings of neutral crown-containing and model styrylheterocycles. Russ. Chem. Bull. Int. Ed. 2009, 58, 1192-1210.
33. Friščić, T.; MacGillivray, L. R. Cyclophanes and ladderanes: Molecular targets for supramolecular chemists. Supramol. Chem. 2005, 17, 47-51.
34. MacGillivray, L. R.; Papaefstathiou, G. S.; Friščić, T.; Hamilton, T. D.; Bučar, D.-K.; Chu, Q.; Varshney, D. B.; Georgiev, I. G. Supramolecular control of reactivity in the solid state: From templates to ladderanes to metal-organic frameworks. Acc. Chem. Res. 2008, 41, 280-291.
35. MacGillivray, L. R. Organic synthesis in the solid state via hydrogen-bond-driven self-assembly. J. Org. Chem. 2008, 73, 3311-3317.
36. Nagarathinam, M.; Vittal, J. J. A rational approach to crosslinking of coordination polymers using the photochemical [2+2] cycloaddition reaction. Macromol. Rapid Commun. 2006, 27, 1091-1099.
37. Nagarathinam, M.; Peedikakkal, A. M. P.; Vittal, J. J. Stacking of double bonds for photochemical [2+2] cycloaddition reactions in the solid state. Chem. Commun. 2008, 5277-5288.
38. Han, Y.-F.; Lin, Y.-J.; Jia, W.-G.; Wang, G.-L.; Jin, G.-X. Template-controlled topochemical photodimerization based on "organometallic macrocycles" through single-crystal to single-crystal transformation. Chem. Commun. 2008, 1807-1809.
39. Han, Y.-F.; Jia, W.-G.; Yu, W.-B.; Jin, G.-X. Stepwise formation of organometallic macrocycles, prisms and boxes from Ir, Rh and Ru-based half-sandwich units. Chem. Soc. Rev. 2009, 38, 3419-3434.
40. Zhang, W.-Z.; Han, Y.-F.; Lin, Y.-J.; Jin, G.-X. [2+2] Photodimerization in the solid state aided by molecular templates of rectangular macrocycles bearing oxamidato ligands. Organometallics 2010, 29, 2842-2849.
41. Hasegawa, M. Photopolymerization of diolefin crystals. Chem. Rev. 1983, 83, 507-518.
42. Hasegawa, M. Photodimerization and photopolymerization of diolefin crystals. Adv. Phys. Org. Chem. 1995, 30, 117-171.
43. Cohen, M. D.; Elgavi, A.; Green, B. S.; Ludmer, Z.; Schmidt, G. M. J. Photodimerization and excimer emission in a crystalline 1, 4-diphenylbutadiene. J. Am. Chem. Soc. 1972, 94, 6776-6779.
44. Singh, A. K.; Krishna, T. S. R. Fluorescence and photodimerization studies of cyano-substituted diphenylbutadienes. J. Phys. Chem. A 1997, 101, 3066-3069.
45. Sonoda, Y.; Miyazawa, A.; Hayashi, S.; Sakuragi, M. Intermolecular [2+2] photocycloaddition of formyl-and cyano-substituted diphenylhexatrienes in the solid state. Chem. Lett. 2001, 30, 410-411.
46. Drenth, W.; Wiebenga, E. H. Structure of α, ω- diphenylpolyenes. 1. Crystal data of 1,4-diphenyl-1,3-butadiene, 1,6-diphenyl-1,3,5-hexatriene and 1,8-diphenyl-1,3,5,7-octatetraene. Recl. Trav. Chim. Pays-Bas 1953, 72, 39-43.
47. Glaser, R.; Dendi, L. R.; Knotts, N.; Barnes, C. L. Ab initio and crystal structures of (E,E)-1,4-diphenylbutadiene: A new type of arene-arene double T-contact and an interesting interlayer cooperation involving diastereoisomeric contacts. Cryst. Growth Des. 2003, 3, 291-300.
48. Gavezzotti, A.; Desiraju, G. R. A systematic analysis of packing energies and other packing parameters for fused-ring aromatic hydrocarbons. Acta Crystallogr. 1988, B44, 427-434.
49. Desiraju, G. R.; Gavezzotti, A. Crystal structures of polynuclear aromatic hydrocarbons. Classification, rationalization and prediction from molecular structure. Acta Crystallogr. 1989, B45, 473-482.
50. Hall, T.; Bachrach, S. M.; Spangler, C. W.; Sapochak, L. S.; Lin, C. T.; Guan, H. W.; Rogers, R. D. Structure of all-trans-1,6-diphenyl-(A) and all-trans-1,6-bis (o-methoxyphenyl)-1,3,5-hexatriene (B). Acta Crystallogr. 1989, C45, 1541-1543.
51. Sonoda, Y.; Morii, H.; Sakuragi, M.; Suzuki, Y. Substituent effect on the cis-trans photoisomerization of trans, trans, trans-1, 6-diphenyl-1, 3, 5-hexatrienes. Chem. Lett. 1998, 27, 349-350.
52. Sonoda, Y.; Kwok, W. M.; Petrasek, Z.; Ostler, R.; Matousek, P.; Towrie, M.; Parker, A. W.; Phillips, D. Solvent effects on the photophysical and photochemical properties of (E, E, E)-1,6-bis (4-nitrophenyl) hexa-1,3,5-triene. J. Chem. Soc. Perkin Trans. 2 2001, 308-314.
53. The crystal structures of 4 and 7 are to be published elsewhere.
54. Reddy, D. S.; Goud, B. S.; Panneerselvam, K.; Desiraju, G. R. C-H... N mediated hexagonal network in the crystal structure of the 1:1 molecular complex 1, 3, 5-tricyanobenzenehexamethylbenzene. J. Chem. Soc. Chem. Commun. 1993, 663-664.
55. Desiraju, G. R. Supramolecular synthons in crystal engineering-A new organic synthesis. Angew. Chem. Int. Ed. Engl. 1995, 34, 2311-2327.
56. Desiraju, G. R. Designer crystals: Intermolecular interactions, network structures and supramolecular synthons. Chem. Commun. 1997, 1475-1482.
57. Nangia, A.; Desiraju, G. R. Supramolecular structures - reason and imagination. Acta Crystallogr. 1998, A54, 934-944.
58. Dhurjati, M. S. K.; Sarma, J. A. R. P.; Desiraju, G. R. Unusual [2+2] topochemical cycloadditions of 3-cyano-and 4-cyano-cinnamic acids: Temperature dependent solid state photochemical reactions. J. Chem. Soc. Chem. Commun. 1991, 1702-1703.
59. Sonoda, Y.; Kawanishi, Y.; Ikeda, T.; Goto, M.; Hayashi, S.; Yoshida, Y.; Tanigaki, N.; Yase, K. Fluorescence spectra for the microcrystals and thin films of trans, trans, trans-1, 6-diphenyl-1, 3, 5-hexatrienes. J. Phys. Chem. B 2003, 107, 3376-3383.
60. Sonoda, Y.; Suzuki, Y. Stereoselective Z, E-photoisomerization of formyl-substituted (E, E, E)-1,6-diphenylhexa-1,3,5-triene in solution. J. Chem. Soc. Perkin Trans. 2 1996, 401-404.
61. Sonoda, Y.; Suzuki, Y. Solvent-dependent cis-trans one-way photoisomerization of bisformylsubstituted 1, 6-diphenyl-1, 3, 5-hexatriene. Chem. Lett. 1996, 25, 659-660.
62. Sonoda, Y.; Kawanishi, Y.; Sakuragi, M. A heavy-atom effect on the cis-trans photoisomerization of bisforlmyl-substituted trans, trans, trans-1, 6-diphenyl-1, 3, 5-hexatriene. Chem. Lett. 1999, 28, 587-588.
63. Sarma, J. A. R. P.; Desiraju, G. R. The role of Cl... Cl and C-H... O interactions in the crystal engineering of 4-A short-axis structures. Acc. Chem. Res. 1986, 19, 222-228.
64. Desiraju, G. R. The C-H... O hydrogen bond in crystals: What is it? Acc. Chem. Res. 1991, 24, 290-296.
65. Desiraju, G. R. The C-H... O hydrogen bond: Structural implications and supramolecular design. Acc. Chem. Res. 1996, 29, 441-449.
66. Steiner, T.; Desiraju, G. R. Distinction between the weak hydrogen bond and the van der Waals interaction. Chem. Commun. 1998, 891-892.
67. Desiraju, G. R. Hydrogen bridges in crystal engineering: Interactions without borders. Acc. Chem. Res. 2002, 35, 565-573.
68. Desiraju, G. R. C-H... O and other weak hydrogen bonds. From crystal engineering to virtual screening. Chem. Commun. 2005, 2995-3001.
69. Nakanishi, F., Nakanishi, H., Tasai, T., Suzuki, Y., Hasegawa, M. Water participation in the crystalline state photoreaction photodimerization of p-formylcinnamic acid. Chem. Lett. 1974, 3, 525-528.
70. Nakanishi, F.; Nakanishi, H.; Tsuchiya, M.; Hasegawa, M. Water-participation in the crystallinestate photodimerization of cinnamic acid derivatives. A new type of organic photoreaction. Bull. Chem. Soc. Jpn. 1976, 49, 3096-3099.
71. Ghosh, U.; Misra, T. N. Spectroscopic studies of photochemical reactions in organic solids. Photodimerization of p-formylcinnamic acid. Bull. Chem. Soc. Jpn. 1985, 58, 2403-2406.
72. 3, a photodimerizable crystal. Acta Crystallogr. 1985, C41, 70-71.
73. Sharma, C. V. K.; Desiraju, G. R. C-H... O hydrogen bond patterns in crystalline nitro compounds: Studies in solid-state molecular recognition. J. Chem. Soc. Perkin Trans. 2 1994, 2345-2352.
74. Thaimattam, R.; Xue, F.; Sarma, J. A. R. P.; Mak, T. C. W.; Desiraju, G. R. Inclusion compounds of tetrakis (4-nitrophenyl) methane: C-H... O networks, pseudopolymorphism, and structural transformations. J. Am. Chem. Soc. 2001, 123, 4432-4445.
75. Sonoda, Y.; Kawanishi, Y.; Goto, M. (E, E, E)-1,6-Bis (4-nitrophenyl) hexa-1,3,5-triene. Acta Crystallogr. 2005, E61, o1200-o1202.
76. Sonoda, Y.; Tsuzuki, S.; Goto, M.; Tohnai, N.; Yoshida, M. Fluorescence spectroscopic properties of nitro-substituted diphenylpolyenes: Effects of intramolecular planarization and intermolecular interactions in crystals. J. Phys. Chem. A 2010, 114, 172-182.
77. Desiraju, G. R.; Sharma, C. V. K. M. C-H... O hydrogen bonding and topochemistry in crystalline 3, 5-dinitrocinnamic acid and its 1:1 donor-acceptor complex with 2, 5-dimethoxycinnamic acid. J. Chem. Soc. Chem. Commun. 1991, 1239-1241.
78. Sharma, C. V. K.; Panneerselvam, K.; Shimoni, L.; Katz, H.; Carrell, H. L.; Desiraju, G. R. 3-(3',5'-Dinitrophenyl)-4-(2',5'-dimethoxyphenyl) cyclobutane-1, 2-dicarboxylic acid: Engineered topochemical synthesis and molecular and supramolecular properties. Chem Mater. 1994, 6, 1282-1292.
79. Capparelli, M. V.; Codding, P. W. Photodimerization of α, ω-diarylbutadienes. I. Crystal and molecular structures of trans, trans-l-(2'-methoxyphenyl)-4-(4'-nitrophenyl)-1,3-butadiene and its photodimer. Can. J. Chem. 1993, 71, 942-950.
80. Mascitti, V.; Corey, E. J. Photochemical studies on ladderane formation from conjugated esters in solution or solid phase. Tetrahedron Lett. 2006, 47, 5879-5882.
81. Sonoda, Y.; Goto, M.; Tsuzuki, S.; Tamaoki, N. Fluorescence spectroscopic properties and crystal structure of a series of donor-acceptor diphenylpolyenes. J. Phys. Chem. A 2006, 110, 13379-13387.
82. Sonoda, Y.; Kawanishi, Y. Solvent-dependent cis-trans photoisomerization of p-methoxy-p'-nitro-substituted trans, trans, trans-1, 6-diphenyl-1, 3, 5-hexatriene. Chem. Lett. 2003, 32, 978-979.
83. Sarma, J. A. R. P.; Desiraju, G. R. The chloro-substituent as a steering group: A comparative study of non-bonded interactions and hydrogen bonding in crystalline chloro-aromatics. Chem. Phys. Lett. 1985, 117, 160-164.
84. Desiraju, G. R.; Parthasarathy, R. The nature of halogen...halogen interactions: Are short halogen contacts due to specific attractive forces or due to close packing of nonspherical atoms? J. Am. Chem. Soc. 1989, 111, 8725-8726.
85. Pedireddi, V. R.; Reddy, D. S.; Goud, B. S.; Craig, D. C.; Rae, A. D.; Desiraju, G. R. The nature of halogen...halogen interactions and the crystal structure of 1, 3, 5, 7-tetraiodoadamantane. J. Chem. Soc. Perkin Trans. 2 1994, 2353-2360.
86. Reddy, C. M.; Kirchner, M. T.; Gundakaram, R. C.; Padmanabhan, K. A.; Desiraju, G. R. Isostructurality, polymorphism and mechanical properties of some hexahalogenated benzenes: The nature of halogen...halogen interactions. Chem. Eur. J. 2006, 12, 2222-2234.
87. Bui, T. T. T.; Dahaoui, S.; Lecomte, C.; Desiraju, G. R.; Espinosa, E. The nature of halogen...halogen interactions: A model derived from experimental charge-density analysis. Angew. Chem. Int. Ed. 2009, 48, 3838-3841.
88. Sarma, J. A. R. P.; Desiraju, G. R. Crystal engineering via Cl... Cl non-bonded interactions. The novel 2:1 complex, 6-chloro-3,4-(methylenedioxy) cinnamic acid-2,4-dichlorocinnamic acid. Topochemical conversion into an unsymmetrical cyclobutane and kinetics of the reaction. J. Chem. Soc. Chem. Commun. 1984, 145-147.
89. Cohen, M. D.; Green, B. S.; Ludmer, Z.; Schmidt, G. M. J. Excimer emission and photodimerization in a crystalline stilbene. Chem. Phys. Lett. 1970, 7, 486-490.
90. Cohen, R.; Ludmer, Z.; Yakhot, V. Structural influence on the excimer emission from a dimorphic crystalline stilbene. Chem. Phys. Lett. 1975, 34, 271-274.
91. Elgavi, A.; Green, B. S.; Schmidt, G. M. J. Reactions in chiral crystals. Optically active heterophotodimer formation from chiral single crystals. J. Am. Chem. Soc. 1973, 95, 2058-2059.
92. Green, B. S.; Heller, L. Solution and solid-state photodimerization of some styrylthiophenes. J. Org. Chem. 1974, 39, 196-201.
93. Warshel, A.; Shakked, Z. Theoretical study of excimers in crystals of flexible conjugated molecules. Excimer formation and photodimerization in crystalline 1, 4-diphenylbutadiene. J. Am. Chem. Soc. 1975, 97, 5679-5684.
94. Sonoda, Y.; Kawanishi, Y.; Goto, M. (E, E, E)-1,6-Bis (2,4-di-chloro-phenyl)-hexa-1,3,5-triene. Acta Crystallogr. 2003, C59, o311-o313.
95. Thalladi, V. R.; Weiss, H.-C.; Bläser, D.; Boese, R.; Nangia, A.; Desiraju, G. R. C-H... F interactions in the crystal structures of some fluorobenzenes. J. Am. Chem. Soc. 1998, 120, 8702-8710.
96. Desiraju, G. R. Crystal engineering: A holistic view. Angew. Chem. Int. Ed. 2007, 46, 8342-8356.
97. Kumar, V. A.; Begum, N. S.; Venkatesan, K. Crystal engineering: Fluorine as a new steering group. J. Chem. Soc. Perkin Trans. 2 1993, 463-467.
98. Vishnumurthy, K.; Guru Row, T. N.; Venkatesan, K. Studies in crystal engineering: Effect of fluorine substitution in crystal packing and topological photodimerization of styryl coumarins in the solid state. J. Chem. Soc. Perkin Trans. 2 1996, 1475-1478.
99. Vishnumurthy, K.; Guru Row, T. N.; Venkatesan, K. Studies in crystal engineering: Crystal packing, topological photodimerization and structure-reactivity correlations in fluoro-substituted styrylcoumarins. J. Chem. Soc. Perkin Trans. 2 1997, 615-619.
100. Vishnumurthy, K.; Guru Row, T. N.; Venkatesan, K. Unusual photodimerization of 7-fluoro-4-methylcoumarin and 6-fluoro-4-methylcoumarin in the solid state. Tetrahedron 1998, 54, 11235-11246.
101. Vishnumurthy, K.; Guru Row, T. N.; Venkatesan, K. Studies in crystal engineering: Steering ability of fluorine in 4-styrylcoumarins. Tetrahedron 1999, 55, 4095-4108.
102. Mori, Y.; Matsumoto, A. Photodimerization mechanism of bis (3,4,5-trifluorobenzyl) (E, E)-muconate in a columnar assembly in the crystalline state. Chem. Lett. 2007, 36, 510-511.
103. Mori, Y.; Matsumoto, A. Molecular stacking and photoreactions of fluorine-substituted benzyl muconates in the crystals. Cryst. Growth Des. 2007, 7, 377-385.
104. Cozzi, F.; Ponzini, F.; Annunziata, R.; Cinquini, M.; Siegel, J. S. Polar interactions between stacked π systems in fluorinated 1, 8-diarylnaphthalenes: Importance of quadrupole moments in molecular recognition. Angew. Chem. Int. Ed. Engl. 1995, 34, 1019-1020.
105. Cozzi, F.; Siegel, J. S. Interaction between stacked aryl groups in 1, 8-diarylnaphthalenes: Dominance of polar/π over charge-transfer effects. Pure Appl. Chem. 1995, 67, 683-689.
106. Adams, H.; Blanco, J.-L. J.; Chessari, G.; Hunter, C. A.; Low, C. M. R.; Sanderson, J. M.; Vinter, J. G. Quantitative determination of intermolecular interactions with fluorinated aromatic rings. Chem. Eur. J. 2001, 7, 3494-3503.
107. Gung, B. W.; Patel, M.; Xue, X. A threshold for charge transfer in aromatic interactions? A quantitative study of π-stacking interactions. J. Org. Chem. 2005, 70, 10532-10537.
108. Reichenbächer, K.; Süss, H. I.; Hulliger, J. Fluorine in crystal engineering-"the little atom that could". Chem. Soc. Rev. 2005, 34, 22-30.
109. Gung, B. W.; Xue, X.; Zou, Y. Enthalpy (ΔH) and entropy (ΔS) for π-stacking interactions in near-sandwich configurations: Relative importance of electrostatic, dispersive, and chargetransfer effects. J. Org. Chem. 2007, 72, 2469-2475.
110. Brock, C. P.; Naae, D. G.; Goodhand, N.; Hamor, T. A. A statistical comparison of two determinations of the crystal structure of 2, 3, 4, 5, 6-pentafluorobiphenyl, a molecule forming mixed stacks in the solid state. Acta Crystallogr. 1978, B34, 3691-3696.
111. Naae, D. G. Biphenyl-perfluorobiphenyl; 1:1 molecular complex. Acta Crystallogr. 1979, B35, 2765-2768.
112. Bartholomew, G. P.; Bazan, G. C.; Bu, X.; Lachicotte, R. J. Packing modes of distyrylbenzene derivatives. Chem. Mater. 2000, 12, 1422-1430.
113. Bartholomew, G. P.; Bu, X.; Bazan, G. C. Preferential cocrystallization among distyrylbenzene derivatives. Chem. Mater. 2000, 12, 2311-2318.
114. Feast, W. J.; Lövenich, P. W.; Puschmann, H.; Taliani, C. Synthesis and structure of 4, 4'-bis (2, 3, 4, 5, 6-pentafluorostyryl) stilbene, a self-assembling J aggregate based on aryl-fluoroaryl interactions. Chem. Commun. 2001, 505-506.
115. Bunz, U. H. F.; Enkelmann, V. Structure elucidation, packing, and solid-state behavior of the eglinton - Galbraith dimer. Chem. Eur. J. 1999, 5, 263-266.
116. Nishinaga, T.; Nodera, N.; Miyata, Y.; Komatsu, K. Dehydro[12]-and-[18] annulenes fused with tetrafluorobenzene: Synthesis, electronic properties, packing structures, and reactivity in the solid state. J. Org. Chem. 2002, 67, 6091-6096.
117. Ponzini, F.; Zagha, R.; Hardcastle, K.; Siegel, J. S. Phenyl/pentafluorophenyl interactions and the generation of ordered mixed crystals: sym-Triphenethynylbenzene and symtris (perfluorophenethynyl) benzene. Angew. Chem. Int. Ed. 2000, 39, 2323-2325.
118. Watt, S. W.; Dai, C.; Scott, A. J.; Burke, J. M.; Thomas, R. L.; Collings, J. C.; Viney, C.; Clegg, W.; Marder, T. B. Structure and phase behavior of a 2:1 complex between arene-and fluoroarenebased conjugated rigid rods. Angew. Chem. Int. Ed. 2004, 43, 3061-3063.
119. Smith, C. E.; Smith, P. S.; Thomas, R. L.; Robins, E. G.; Collings, J. C.; Dai, C.; Scott, A. J.; Borwick, S.; Batsanov, A. S.; Watt, S. W.; Clark, S. J.; Viney, C.; Howard, J. A. K.; Clegg, W.; Marder, T. B. Arene-perfluoroarene interactions in crystal engineering: Structural preferences in polyfluorinated tolans. J. Mater. Chem. 2004, 14, 413-420.
120. Coates, G. W.; Dunn, A. R.; Henling, L. M.; Ziller, J. W.; Lobkovsky, E. B.; Grubbs, R. H. Phenylperfluorophenyl stacking interactions: Topochemical [2+2] photodimerization and photopolymerization of olefinic compounds. J. Am. Chem. Soc. 1998, 120, 3641-3649.
121. Vishnumurthy, K.; Guru Row, T. N.; Venkatesan, K. Fluorine in crystal engineering: Photodimerization of (1E, 3E)-1-phenyl-4-pentafluorophenylbuta-1,3- dienes in the crystalline state. Photochem. Photobiol. Sci. 2002, 1, 427-430.
122. Sonoda, Y.; Goto, M.; Tsuzuki, S.; Tamaoki, N. Fluorinated diphenylpolyenes:Crystal structures and emission properties. J. Phys. Chem. A 2007, 111, 13441-13451.
123. Sonoda, Y.; Goto, M.; Tsuzuki, S.; Akiyama, H.; Tamaoki, N. [2+2] Photodimerization and photopolymerization of diphenylhexatriene crystals utilizing perfluorophenyl-phenyl stacking interactions. J. Fluorine Chem. 2009, 130, 151-157.
124. Coates, G. W.; Dunn, A. R.; Henling, L. M.; Dougherty, D. A.; Grubbs, R. H. Phenylperfluorophenyl stacking interactions: A new strategy for supermolecule construction. Angew. Chem. Int. Ed. Engl. 1997, 36, 248-251.
125. Xu, R.; Gramlich, V.; Frauenrath, H. Alternating diacetylene copolymer utilizing perfluorophenyl-phenyl interactions. J. Am. Chem. Soc. 2006, 128, 5541-5547.
126. Liu, J.; Murray, E. M.; Young Jr., V. G. π-Stacking interactions in some crystalline cisoid E, E-1, 4-diaryl-1, 3-butadienes. Chem. Commun. 2003, 1904-1905.
127. Caronna, T.; Liantonio, R.; Logothetis, T. A.; Metrangolo, P.; Pilati, T.; Resnati, G. Halogen bonding and π...π stacking control reactivity in the solid state. J. Am. Chem. Soc. 2004, 126, 4500-4501.
128. Frontera, A.; Quiñonero, D.; Costa, A.; Ballester, P.; Deyà, P. M. MP2 study of cooperative effects between cation-π, anion-π and π-π interactions. New J. Chem. 2007, 31, 556-560.
129. Liu, J.; Boarman, K. J. Regiospecific topochemical reactions controlled by trifluoromethyl directing groups. Chem. Commun. 2005, 340-341.
130. Liu, J.; Wendt, N. L.; Boarman, K. J. Trifluoromethyl groups in crystal design of 1, 4-diphenyl-1, 3-butadienes for topochemical [2 + 2] photodimerization. Org. Lett. 2005, 7, 1007-1010.
131. 3-substituted tetrathiafulvalene derivatives. Chem. Eur. J. 2006, 12, 2994-3005.
132. Hayashi, S.; Sonoda. Y. Two-dimensional 1H spin-exchange NMR study of molecular arrangements in diphenylhexatrienes. Bull. Chem. Soc. Jpn. 2004, 77, 2159-2164.
133. Turowska-Tyrk, I.; Grzesniak, K.; Trzop, E.; Zych, T. Monitoring structural transformations in crystals. Part 4. Monitoring structural changes in crystals of pyridine analogs of chalcone during [2+2]-photodimerization and possibilities of the reaction in hydroxy derivatives. J. Solid State Chem. 2003, 174, 459-465.
134. Mahon, M. F.; Raithby, P. R.; Sparkes, H. A. Investigation of the factors favouring solid state [2 + 2] cycloaddition reactions; the [2 + 2] cycloaddition reaction of coumarin-3-carboxylic acid. CrystEngCommunity 2008, 10, 573-576.
135. Yang, S.-Y.; Naumov, P.; Fukuzumi, S. Topochemical limits for solid-state photoreactivity by fine tuning of the π-π interactions. J. Am. Chem. Soc. 2009, 131, 7247-7249.
136. Abdel-Mottaleb, M. M. S.; De Feyter, S.; Gesquière, A.; Sieffert, M.; Klapper, M.; Müllen, K.; De Schryver, F. C. Photodimerization of cinnamate derivatives studied by STM. Nano Lett. 2001, 1, 353-359.
137. Marubayashi, N.; Ogawa, T.; Hamasaki, T.; Hirayama, N. A buffer zone in the crystal structure that governs the solid-state photodimerization of bulky olefins with the 1, 4-dihydropyridine skeleton. J. Chem. Soc. Perkin Trans. 2 1997, 1309-1314.
138. Gnanaguru, K.; Ramasubbu, N.; Venkatesan, K.; Ramamurthy, V. Topochemical solid state photodimerization of non-ideally oriented monomers: 7-Chlorocoumarin and 7-methoxycoumarin. J. Photochem. 1984, 27, 355-362.
139. Bhadbhade, M. M.; Murthy, G. S.; Venkatesan, K.; Ramamurthy, V. Topochemical dimerization of non-parallel double bonds: 7-Methoxycoumarin. Chem. Phys. Lett. 1984, 109, 259-263.
140. Gnanaguru, K.; Ramasubbu, N.; Venkatesan, K.; Ramamurthy, V. A Study on the photochemical dimerization of coumarins in the solid state. J. Org. Chem. 1985, 50, 2337-2346.
141. Liang, Y.-L.; Fang, J.-M.; Chow, T.; Ho, T.-I.; Lee, C.-R.; Wang, Y. Solution and solid-state photochemistry of 2-anilino-5-phenyl-2, 4-pentadienenitriles. J. Org. Chem. 1994, 59, 5742-5747.
142. Fonseca, I.; Hayes, S. E.; Bertmer, M. Size effects of aromatic substitution in the ortho position on the photodimerization kinetics of α-trans cinnamic acid derivatives. A solid-state NMR study. Phys. Chem. Chem. Phys. 2009, 11, 10211-10218.
143. Xu, L.-P.; Yan, C.-J.; Wan, L.-J.; Jiang, S.-G.; Liu, M.-H. Light-induced structural transformation in self-assembled monolayer of 4-(amyloxy) cinnamic acid investigated with scanning tunneling microscopy. J. Phys. Chem. B 2005, 109, 14773-14778.
144. Swiatkiewicz, J.; Eisenhardt, G.; Prasad, P. N.; Thomas, J. M.; Jones, W.; Theocharis, C. R. Phonon spectroscopy of photochemical reactions in organic solids: Photodimerization of 2-benzyl-5-benzylidenecyclopentanone and photopolymerization of 2, 5-distyrylpyrazine. J. Phys. Chem. 1982, 86, 1764-1767.
145. Ghosh, M.; Mandal, T. K.; Chakrabarti, S.; Misra, T. N. Spectroscopic study of solid-state photoreaction in organic crystals: Photopolymerization of the dimethyl ester of p-phenylenediacrylic acid. J. Raman Spectrosc. 1998, 29, 807-811.
146. Eckhardt, C. J.; Luty, T.; Peachey, N. M. Collective interactions and solid state reactivity. Mol. Cryst. Liq. Cryst. 1998, 313, 25-38.
147. Turowska-Tyrk, I. Structural transformations in a crystal during the photochemical reaction of 2-benzyl-5-benzylidenecyclopentanone. Chem. Eur. J. 2001, 7, 3401-3405.
148. Turowska-Tyrk, I. Monitoring structural transformations in crystals. 5. A topotactic [2+2]-photodimerization reaction. Acta Crystallogr. 2003, B59, 670-675.
149. Turowska-Tyrk, I. Structural transformations in organic crystals during photochemical reactions. J. Phys. Org. Chem. 2004, 17, 837-847.
150. Kim, J. H.; Matsuoka, M.; Fukunishi, K. Selective topochemical photoreaction of crystallized 2,3-bis (2-phenylethenyl)-4,5-dicyanopyrazines. Chem. Lett. 1999, 28, 143-144.
151. Natarajan, A.; Mague, J. T.; Venkatesan, K.; Ramamurthy, V. Large molecular motions are tolerated in crystals of diamine double salt of trans-chlorocinnamic acids with trans-1, 2-diaminocyclohexane. Org. Lett. 2005, 7, 1895-1898.
152. Zheng, S.-L.; Pham, O.; Vande Velde, C. M. L.; Gembicky, M.; Coppens, P. Competitive isomerization and dimerization in co-crystals of 1, 1, 6, 6-tetraphenyl-2, 4-hexadiyne-1, 6-diol and sorbic acid: A new look at stereochemical requirements for [2+2] dimerization. Chem. Commun. 2008, 2538-2540.
153. Robinson, M. R.; Wang, S.; Heeger, A. J.; Bazan, G. C. A tetrahedral oligo (phenylenevinylene) molecule of intermediate dimensions: Effect of molecular shape on the morphology and electroluminescence of organic glasses. Adv. Func. Mater. 2001, 11, 413-419.
154. Shirota, Y. Photo-and electroactive amorphous molecular materials-molecular design, syntheses, reactions, properties, and applications. J. Mater. Chem. 2005, 15, 75-93.
155. Nakanishi, F.; Nakanishi, H.; Hasegawa, M.; Yamada, Y. Four-center type photopolymerization in the solid state. VII. Photochemical reaction of m-phenylene diacrylic acid dimethyl ester. J. Polym. Sci. Part A 1975, 13, 2499-2506.
156. Nakanishi, H.; Sasada, Y. The crystal and molecular structure of dimethyl mphenylenediacrylate. Bull. Chem. Soc. Jpn. 1977, 50, 3182-3185.
157. Chakrabarti, S.; Maity, A. K.; Misra, T. N. Spectroscopic study of solid-state photoreaction in organic crystal: Photopolymerization of dimethyl ester of α, α'-dicyano-p-phenylenediacrylic acid and diethyl ester of p-phenylenediacrylic acid. J. Polym. Sci. Part A 1992, 30, 1625-1631.
158. Minsk, L. M.; Smith, J. G.; Van Deusen, W. P.; Wright, J. F. Photosensitive polymers. I. Cinnamate esters of poly (vinyl alcohol) and cellulose. J. Appl. Polym. Sci. 1959, 2, 302-307.
159. Reiser, A.; Egerton, P. L. The mechanism of crosslink formation in solid polyvinylcinnamate and related photopolymers. Photogr. Sci. Eng. 1979, 23, 144-150.
160. Ichimura, K. Preparation of water-soluble photoresist derived from poly (vinyl alcohol). J. Polym. Sci. Part A 1982, 20, 1411-1417.
161. Ichimura, K.; Watanabe, S. Preparation and characteristics of photocrosslinkable poly (vinyl alcohol). J. Polym. Sci. Part A 1982, 20, 1419-1432.
162. Ichimura, K.; Oohara, N. Photosensitive poly (methacrylates) having styrylpyridinium and styrylquinolinium groups. J. Polym. Sci. Part A 1987, 25, 3063-3077.
163. 13C solid-state NMR. Macromolecules 1994, 27, 6998-6999.
164. Cockburn, E. S.; Davidson, R. S.; Pratt, J. E. The photocrosslinking of styrylpyridinium salts via a [2 + 2]-cycloaddition reaction. J. Photochem. Photobiol. A Chem. 1996, 94, 83-88.
165. Guo, M.; Xu, Z.; Wang, X. Photofabrication of two-dimensional quasi-crystal patterns on UV-curable molecular azo glass films. Langmuir 2008, 24, 2740-2745.
166. Chung, C.-M.; Roh, Y.-S.; Cho, S.-Y.; Kim, J.-G. Crack healing in polymeric materials via photochemical [2+2] cycloaddition. Chem. Mater. 2004, 16, 3982-3984.
167. Li, F.; Zhuang, J.; Jiang, G.; Tang, H.; Xia, A.; Jiang, L.; Song, Y.; Li, Y.; Zhu, D. A rewritable optical data storage material system by [2+2] photocycloreversion-photocycloaddition. Chem. Mater. 2008, 20, 1194-1196.
168. Chung, J. W.; You, Y.; Huh, H. S.; An, B.-K.; Yoon, S.-J.; Kim, S. H.; Lee, S. W.; Park, S. Y. Shear-and UV-induced fluorescence switching in stilbenic π-dimer crystals powered by reversible [2+2] cycloaddition. J. Am. Chem. Soc. 2009, 131, 8163-8172.
169. Enkelmann, V.; Wegner, G. Novak, K.; Wagener, K. B. Single-crystal-to- single-crystal photodimerization of cinnamic acid. J. Am. Chem. Soc. 1993, 115, 10390-10391.
170. Enkelmann, V.; Wegner, G.; Novak, K.; Wagener, K. B. Crystal-to-crystal photodimerizations. Mol. Cryst. Liq. Cryst. 1994, 240, 121-126.
171. Takahashi, S.; Miura, H.; Kasai, H.; Okada, S.; Oikawa, H.; Nakanishi, H. Single-crystal-tosingle-crystal transformation of diolefin derivatives in nanocrystals. J. Am. Chem. Soc. 2002, 124, 10944-10945.
172. Bučar, D.-K.; MacGillivray, L. R. Preparation and reactivity of nanocrystalline cocrystals formed via sonocrystallization. J. Am. Chem. Soc. 2007, 129, 32-33.