R. Kadu et al. / Journal of Molecular Structure 1033 (2013) 298–311
311
(1998) 6405;
maximum fluorescence emission intensity probably due to the
dominating + R effects of p-OCH3 groups. The calculated optical
band gaps (Eg) for 1–5 fall in the range of 2.17–3.03 eV, demon-
strating a direct band gap semiconducting nature of these com-
pounds. The extra thermal stability of 3, may be caused by the
presence of extended conjugation and massive number of intermo-
lecular interactions in the solid state.
(c) S.S. Kuduva, D.C. Craig, A. Nangia, G.R. Desiraju, J. Am. Chem. Soc. 121
(1999) 1936.
[9] J.A.A.W. Elemans, A.E. Rowan, R.J.M. Nolte, J. Mater. Chem. 13 (2003) 2661.
[10] G.R. Desiraju, Curr. Opin. Solid State Mater. Sci. 2 (1997) 451.
[11] (a) A.T. Hulme, S.L. Price, D.A. Tocher, J. Am. Chem. Soc. 127 (2005) 1116;
(b) M.T. Kirchner, D. Bläser, R. Boese, Chem. Eur. J. 16 (2010) 2131.
[12] A. Collas, I. Bagrowska, K. Aleksandrzak, M. Zeller, F. Blockhuys, Cryst. Growth
Des. 11 (2011) 1299.
[13] (a) M. Nishio, Tetrahedron 36 (2005) 6923;
(b) H.W. Roesky, M. Andruh, Coord. Chem. Rev. 236 (2003) 91;
(c) S. Bhosale, A.L. Sisson, N. Sakai, S. Matile, Org. Biomol. Chem. 4 (2006) 3031;
(d) B. Bhayana, C.S. Wilcox, Angew. Chem. Int. Ed. 46 (2007) 6833.
[14] L.P. García, D.B. Amabilino, Chem. Soc. Rev. 31 (2002) 342.
[15] P. Przybylski, A. Huczynski, K.G. Bejcar, B. Brzezinski, F. Bartl, Curr. Org. Chem.
13 (2009) 124.
[16] N. Kiriy, V. Bocharova, A. Kiriy, M. Stamm, F.C. Krebs, H.-J. Adler, Chem. Mater.
16 (2004) 4765.
[17] Y. Zheng, K. Ma, H. Li, J. Li, J. He, X. Sun, R. Li, J. Ma, Catal. Lett. 128 (2009) 465.
[18] M. Largeron, M.-B. Fleury, Org. Lett. 11 (2009) 883.
[19] (a) J.A. O’Meara, N. Gardee, M. Jung, R.N. Ben, T. Durst, J. Org. Chem. 63 (1998)
3117;
Acknowledgements
VKS and SKV acknowledge CSIR, India for the financial support
(Project No. 01/(2204)/07/EMR-II). One of the authors, Rahul Kadu
acknowledges UGC, India for the financial support in the form of
fellowship and contingency. We would like to acknowledge Dinesh
Vidhani and Marie E. Krafft for their help in computational study.
Appendix A. Supplementary material
(b) F. Valot, F. Fache, R. Jacquot, M. Spagnol, M. Lemaire, Tetrahedron Lett. 40
(1999) 3689;
Electronic Supplementary Information (ESI) available: Addi-
tional figures and CIF files. See CCDC reference numbers 864035
for 1; 864037 for 2; 782593 for 3; 864036 for 4. Supplementary
data associated with this article can be found, in the online version,
(c) A.K. Szardening, T.S. Burkoth, G.C. Look, D.A. Campbell, J. Org. Chem. 61
(1996) 6720;
(d) C. Chiappe, D. Pieraccini, Green Chem. 5 (2003) 193.
[20] R.N. Salvatore, C.H. Yoon, K.W. Jung, Tetrahedron 57 (2001) 7785.
[21] Oxford Diffraction, CrysAlis PRO, Oxford Diffraction Ltd., Yarnton, England,
2009.
[22] G.M. Sheldrick, SHELXTL Reference Manual: Version 5.1, Bruker AXS, Madison,
WI, 1997.
[23] G.M. Sheldrick, SHELXL-97: Program for Crystal Structure Refinement,
University of Göttingen, Göttingen, Germany, 1997.
References
[24] (a) A. Göbel, G. Leibeling, M. Rudolph, W. Imhof, Organometallics 22 (2003)
759;
(b) H.K. Lee, S.W. Lee, Acta Cryst. E65 (2009) o2263.
[25] X. Tao, H. Cui, Acta Cryst. E65 (2009) o2251.
[26] (a) A. Jarrahpour, M. Zarei, Molecules 12 (2007) 2364;
(b) M. Taneda, K. Amimoto, H. Koyama, T. Kawato, Org. Biomol. Chem. 2 (2004)
499;
[1] S. Glasstone, Trans. Faraday Soc. 33 (1937) 200.
[2] D.J. Sutor, Nature 195 (1962) 68.
[3] D.J. Sutor, J. Chem. Soc. (1963) 1105.
[4] (a) Y. Gu, T. Kar, S. Scheiner, J. Am. Chem. Soc. 121 (1999) 9411;
(b) Z.S. Derewenda, L. Lee, U. Derewenda, J. Mol. Biol. 252 (1995) 248;
(c) G.R. Desiraju, T. Steiner, The Weak Hydrogen Bond: In Structural Chemistry
and Biology, Oxford University Press, New York, 2001;
(d) P. Hobza, Z. Havlas, Chem. Rev. 100 (2000) 4253;
(c) J.M.C.A. Kerckhoffs, J.C. Peberdy, I. Meistermann, L.J. Childs, C.J. Isaac, C.R.
Pearmund, V. Reudegger, S. Khalid, N.W. Alcock, M.J. Hannon, A. Rodger,
Dalton Trans. (2007) 734;
(d) P.D. Mehata, N.P.S. Sengar, E.V.S. Subrahmanyam, D. Satyanarayana, Indian
J. Pharm. Sci. 68 (2006) 103.
(e) G.R. Desiraju, Acc. Chem. Res. 29 (1996) 441;
(f) R. Taylor, O. Kennard, J. Am. Chem. Soc. 104 (1982) 5063.
[5] (a) C.E. Marjo, M.L. Scudder, D.C. Craig, R. Bishop, J. Chem. Soc. Perkin Trans. 2
(1997) 2099;
[27] H. Suezawa, T. Yoshida, M. Hirota, H. Takahashi, Y. Umezawa, K. Honda, S.
Tsuboyama, M. Nishio, J. Chem. Soc. Perkin Trans. 2 (2001) 2053.
[28] C.M.L.V. Velde, H.J. Geise, F. Blockhuys, Cryst. Growth Des. 6 (2006) 241.
[29] M.J. Frisch, G.W. Trucks, H.B. Schlegel, G.E. Scuseria, M.A. Robb, J.R. Cheeseman,
J.A. Montgomery, Jr., T. Vreven, K.N. Kudin, J.C. Burant, J.M. Millam, S.S. Iyengar,
J. Tomasi, V. Barone, B. Mennucci, M. Cossi, G. Scalmani, N. Rega, G.A.
Petersson, H. Nakatsuji, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa,
M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, M. Klene, X. Li, J.E. Knox,
H.P. Hratchian, J.B. Cross, C. Adamo, J. Jaramillo, R. Gomperts, R.E. Stratmann,
O. Yazyev, A.J. Austin, R. Cammi, C. Pomelli, J.W. Ochterski, P.Y. Ayala, K.
Morokuma, G.A. Voth, P. Salvador, J.J. Dannenberg, V.G. Zakrzewski, S.
Dapprich, A.D. Daniels, M.C. Strain, O. Farkas, D.K. Malick, A.D. Rabuck, K.
Raghavachari, J.B. Foresman, J.V. Ortiz, Q. Cui, A.G. Baboul, S. Clifford, J.
Cioslowski, B.B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R.L.
Martin, D.J. Fox, T. Keith, M.A. Al-Laham, C.Y. Peng, A. Nanayakkara, M.
Challacombe, P.M.W. Gill, B. Johnson, W. Chen, M.W. Wong, C. Gonzalez, and
J.A. Pople, Gaussian, Inc., Wallingford, CT, 2004.
[30] (a) K.-H. Lee, C.-S. Choi, K.-S. Jeon, J. Photosci. 9 (2002) 71;
(b) S.C. Martens, U. Zschieschang, H. Wadepohl, H. Klauk, L.H. Gade, Chem. Eur.
J. 18 (2012) 3498;
(c) A.C. Valdés, G.P. -Luis, I.A. Rivero, J. Mex. Chem. Soc. 51 (2007) 87;
(d) D. Madrigal, G.P. Luis, I.A. Rivero, J. Mex. Chem. Soc. 50 (2006) 175.
[31] H. Liu, B. Li, D. Liu, Z. Xu, Chem. Phys. Lett. 350 (2001) 441.
[32] E.A. Davis, N.F. Mott, Phil. Mag. 22 (1970) 903.
(b) V.R. Thalladi, A. Gehrke, R. Boese, New J. Chem. 24 (2000) 463;
(c) M. Mascal, Chem. Commun. (1998) 303;
(d) K.E. Maly, T. Maris, E. Gagnon, J.D. Wuest, Cryst. Growth Des. 6 (2006) 461;
(e) E. Bosch, Cryst. Growth Des. 10 (2010) 3808.
[6] (a) M. Nishio, CrystEngComm 6 (2004) 130;
(b) M. Nishio, Y. Umezawa, K. Honda, S. Tsuboyama, H. Suezawa,
CrystEngComm 11 (2009) 1757;
(c) O. Takahashi, Y. Kohno, M. Nishio, Chem. Rev. 110 (2010) 6049;
(d) S.K. Nayak, R. Sathishkumar, T.N. Guru Row, CrystEngComm 12 (2010)
3112;
(e) O. Takahashi, Y. Kohno, S. Iwasaki, K. Saito, M. Iwaoka, S. Tomoda, Y.
Umezawa, S. Tsuboyama, M. Nishio, Bull. Chem. Soc. Jpn. 74 (2001) 2421;
(f) A.K. Tewari, R. Dubey, Bioorg. Med. Chem. 16 (2008) 126;
(g) Y. Kobayashi, K. Saigo, J. Am. Chem. Soc. 127 (2005) 15054;
(h) K. Saigo, Y. Kobayashi, Chem. Rec. 7 (2007) 47;
(i) P. Sozzani, A. Comotti, S. Bracco, R. Simonutti, Chem. Commun. (2004) 768;
(j) J.P. Hill, R. Scipioni, M. Boero, Y. Wakayama, M. Akada, T. Miyazaki, K. Ariga,
Phys. Chem. Chem. Phys. 11 (2009) 6038;
(k) E.R.T. Tiekink, J.Z. Schpector, The Importance of Pi-Interactions in Crystal
Engineering: Frontiers in Crystal Engineering, John Wiley & Sons Inc., 2012;
(l) M. Nishio, Phys. Chem. Chem. Phys. 13 (2011) 13873;
(m) M. Nishio, J. Mol. Struct. 1018 (2012) 2.
[7] (a) C.A. Hunter, J.K.M. Sanders, J. Am. Chem. Soc. 112 (1990) 5525;
(b) C.A. Hunter, Chem. Soc. Rev. 23 (1994) 101;
[33] (a) M.H. Habibi, N. Talebian, Acta Chim. Slov. 52 (2005) 53;
(b) J. Tauc, Mater. Res. Bull. 5 (1970) 721.
[34] P. Dutta, W. Yang, S.H. Eom, S.-H. Lee, Org. Electron. 13 (2012) 273.
(c) C. Janiak, J. Chem. Soc. Dalton Trans. (2000) 3885;
(d) T.F. Headen, C.A. Howard, N.T. Skipper, M.A. Wilkinson, D.T. Bowron, A.K.
Soper, J. Am. Chem. Soc. 132 (2010) 5735.
[8] (a) G.R. Desiraju, Science 278 (1997) 404;
(b) G. Harakas, T. Vu, C.B. Knobler, M.F. Hawthorne, J. Am. Chem. Soc. 120