Molecular recognition of 2-alkylbenzimidazole: Photophysical and structural studies

Journal of Photochemistry and Photobiology A: Chemistry

Volumn 211, Issue 2-3, 2010, Pages 176-184

  Ojha, Bimlesh ^a   Das, Gopal ^a  

^a INDIAN INSTITUTE OF TECHNOLOGY GUWAHATI   (India)

Author keywords

Co crystal; Electron deficient compound; Electron rich compound; Fluorescence; Organic salt; Supramolecular chemistry

Indexed keywords

EID: 77952011550     PISSN: 10106030     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jphotochem.2010.01.021     Document Type: Article

References (55)

1. Desiraju G.R. Acc. Chem. Res. 2002, 35:565-573.
2. Hobza P., Havlas Z. Chem. Rev. 2000, 100:4253-4264.
3. Steiner T., Saenger W. J. Chem. Soc., Chem. Commun. 1995, 20:2087-2088.
4. Thallapally P.K., Katz A.K., Carrell H.L., Desiraju G.R. Cryst. Eng. Commun. 2003, 5:87-92.
5. Schmuck C., Lex J. Eur. J. Org. Chem. 2001, 8:1519-1523.
6. Huggins M.T., Lightner D.A. J. Org. Chem. 2001, 66:8402-8410.
7. Marques M.P.M., da Costa A.M.A., Ribeiro-Claro P.J.A. J. Phys. Chem. A 2001, 105:5292-5297.
8. Sutor D.J. Nature 1962, 195:68-69.
9. Desiraju G.R., Steiner T. The Weak Hydrogen Bonds in Structural Chemistry and Biology 1999, Oxford University Press, Oxford.
10. Meyer E.A., Castellano R.A., Diederich F. Angew. Chem. Int. Ed. Engl. 2003, 42:4120.
11. Prins L.J., Reinhoudt D.N., Timmerman P. Angew. Chem. Int. Ed. Engl. 2001, 40:2382-2426.
12. Frederik C.K., Mikkel J. J. Org. Chem. 2001, 66:6169-6173.
13. Weber E. Design of Organic Solids: Topics in Current Chemistry 1998, Springer, Berlin.
14. Bhogala B.R. Cryst. Growth Des. 2003, 3:547-554.
15. Zhang X.L., Chen X.M. Cryst. Growth Des. 2005, 5:617-622.
16. Pedireddi V.R., Chatterjee S., Ranganathan A., Rao C.N.R. J. Am. Chem. Soc. 1997, 119:10867-10868.
17. Shattock T.R., Vishweshwar P., Wang Z.Q., Zaworotko M.J. Cryst. Growth Des. 2005, 5:2046-2049.
18. Bhogala B.R., Basavoju S., Nangia A. Cryst. Growth Des. 2005, 5:1683-1686.
19. Sarkar M., Biradha K. Cryst. Growth Des. 2006, 6:202-208.
20. Bhatt P.M., Ravindra N.V., l Banerjeea R., Desiraju G.R. Chem. Commun. 2005, 8:1073-1075.
21. Desiraju G.R. Cryst. Eng. Commun. 2003, 5:466-467.
22. Lin S.N., Yang L. Tetrahedron Lett. 2005, 46:4315-4319.
23. Valdez J., Cedillo R., Campos A.H., Yepez L., Luis F.H., Vazquez G.N., Tapia A., Cortes R., Hernandezc M., Castillo R. Bioorg. Med. Chem. Lett. 2002, 12:2221-2224.
24. Xue G., Zhang J., Shi G., Wu Y., Shuen B. J. Chem. Soc., Perkin Trans. 1989, 2:33-36.
25. Chen Z., Xu D.J., Li Z.Y., Wu J.Y., Chiang M.Y. J. Coord. Chem. 2003, 56:253-259.
26. Su J.R., Xu D.J. J. Coord. Chem. 2004, 57:223-229.
27. Alamgir M., Black D.C., Kumar N. Topics in Heterocyclic chemistry 2007, Springer, Berlin/Heidelberg.
28. Akutagawa T., Hasegawa T., Nakamura T., Saito G. Cryst. Eng. Commun. 2003, 5:54-57.
29. Ferrer J.R., Lahti P.M., George C., Oliete P., Julier M., Palacio F. Chem. Mater. 2001, 13:2447-2454.
30. Lahti P.M., Ferrer J.R., George C., Oliete P., Julier M., Palacio F. Polyhedron 2001, 20:1465-1473.
31. Liu Z., Chen Y., Liu P., Wang J., Huang M. J. Solid State Chem. 2005, 178:2306-2312.
32. Chowdhury P., Panja S., Chatterjee A., Bhattacharya P., Chakravorti S. J. Photochem. Photobiol. 2005, 170:131-141.
33. Krishnamurthy M., Phaniraj P., Dogra S.K. J. Chem. Soc. Perkin Trans. 1986, 2:1917-1925.
34. Pramanik A., Das G. Cryst. Growth Des. 2008, 8:3107-3113.
35. Pramanik A., Bhuyan M., Das G. J. Photochem. Photobiol. A 2008, 197:149-155.
36. Thakuria H., Borah B.M., Pramanik A., Das G. Tetrahedron Lett. 2006, 47:3135-3138.
37. Pramanik A., Bhuyan M., Choudhury R., Das G. J. Mol. Struct. 2008, 879:88-95.
38. Thakuria H., Borah B.M., Pramanik A., Das G. J. Chem. Crystallogr. 2007, 37:807-816.
39. Seka R., Muller R.H. Monatsh, Chem. 1931, 57:95.
40. Pool W.O., Harwood J.H., Ralston A.W. J. Am. Chem. Soc. 1937, 59:178-179.
41. Hui Z.Z., Liang Y., Mei W.Y. Catal. Commun. 2007, 8:1126-1131.
42. SMART, SAINT and XPREP, Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA, 1995.
43. Sheldrick G.M. SADABS: software for Empirical Absorption Correction 1999-2003, University of Gottingen, Institute fur Anorganische Chemieder Universitat, Tammanstrasse 4, D-3400 Gottingen, Germany.
44. Sheldrick G.M. SHELXS-97 1997, University of Gottingen, Germany.
45. Farrugia L.J. J. Appl. Crystallogr. 1997, 30:565.
46. Kondo M., Kuwano H. Bull. Chem. Soc. Jpn. 1969, 42:1433-1435.
47. Rogers K.S., Clayton C.C. Anal. Biochem. 1972, 48:199-201.
48. Lakowicz J.R. Principles of Fluorescence spectroscopy 1999, Kluwer Academic/Plenum, New York. 2nd ed.
49. Cielen E., Tahri A., Heyen K.V., Hoornaert G.J., De Schryver F.C., Boens N. J. Chem. Soc. Perkin Trans. 1998, 2:1573-1580.
50. Prasanna de Silva A., Nimal Gunaratne H.Q. J. Chem. Soc., Chem. Commun. 1990, 2:186-188.
51. Jose D.A., Kumar D.K., Ganguly B., Das A. Tetrahedron Lett. 2005, 46:5343-5346.
52. Ghosh K., Masanta G. Tetrahedron Lett. 2008, 49:2592-2597.
53. Ghosh K., Sena T., Frohlichb R. Tetrahedron Lett. 2007, 48:7022-7026.
54. Shao J., Qiao Y., Lin H., Lin H. J. Fluoresc. 2009, 19:183-188.
55. Crystal data for L1: C11H13N2, CCDC #736542; M=173.23, orthorhombic, a=8.5337(4), b=9.8356(4), c=24.4752(13)Å, V=2054.30(17)Å3, space group Pbca, Z=8, T=298(2)K, μ (Mo-Kα)=0.065mm-1, F(000)=837, GOF=1.076; final R indices: R1=0.0481 [I>2σ(I)], wR2=0.2060; R indices (all data): R1=0.0896, wR2=0.2302. L2: C16H24N2, CCDC #736543; M=244.37, orthorhombic, a=9.9382(7), b=35.996(2), c=8.7463(5)Å, V=3128.9(4)Å3, space group Pbca, Z=8, T=298(2)K, μ (Mo-Kα)=0.062mm-1, F(000)=1080, GOF=1.078; final R indices: R1=0.0724 [I>2σ(I)], wR2=0.1128; R indices (all data): R1=0.0966, wR2=0.1616. L3: C18H28N2, CCDC #736544; M=272.42, orthorhombic, a=7.700(3), b=9.950(4), c=44.635(18)Å, V=3420(2)Å3, space group Pbca, Z=8, T=298(2)K, μ (Mo-Kα)=0.060mm-1, F(000)=1200, GOF=0.978; final R indices: R1=0.0708 [I>2σ(I)], wR2=0.2079; R indices (all data): R1=0.0939, wR2=0.2247. Salt 1: C14H18N2O4, CCDC #736545; M=278.30, monoclinic, a=17.9579(9), b=9.5211(5), c=8.5216(5)Å, V=1399.51(13)Å3, space group Cc, Z=4, T=298(2)K, μ (Mo-Kα)=0.096mm-1, F(000)=568, GOF=1.049; final R indices: R1=0.0553 [I>2σ(I)], wR2=0.1448; R indices (all data): R1=0.0607, wR2=0.1505. Salt 2: C18H22N2O3S, CCDC #736546; M=346.45, orthorhombic, a=16.2967(8), b=51.504(3), c=9.2908(5)Å, V=7798.2(7)Å3, space group Fdd2, Z=16, T=298(2)K, μ (Mo-Kα)=0.181mm-1, F(000)=2816, GOF=1.100; final R indices: R1=0.0547 [I>2σ(I)], wR2=0.1822; R indices (all data): R1=0.0772, wR2=0.2104. Salt 3: C32H34N4O8, CCDC #736547; M=602.63, triclinic, a=13.5327(4), b=18.9009(5), c=20.1113(5)Å, V=4594.8(2)Å3, space group P-1, Z=4, T=298(2)K, μ (Mo-Kα)=0.063 mm-1, F(000)=1892, GOF=1.022; final R indices: R1=0.0779 [I _ 2σ(I)], wR2=0.1728; R indices (all data): R1=0.0924, wR2=0.2146. Salt 4: C19H28N2O4, CCDC #736548; M=348.43, triclinic, a=5.3488(4), b=9.5569(7), c=19.1994(16)Å, V=963.43(13)Å3, space group P-1, Z=2, T=298(2)K, μ (Mo-Kα)=0.082mm-1, F(000)=360, GOF=0.926; final R indices: R1=0.0607 [I>2σ(I)], wR2=0.1251; R indices (all data): R1=0.0942, wR2=0.1971. Salt 5: C84H105N8O16, CCDC #736549; M=1482.76, triclinic, a=12.8838(4), b=16.4270(5), c=19.2316(5)Å, V=4024.0(2)Å3, space group P-1, Z=2, T=298(2)K, μ (Mo-Kα)=0.088mm-1, F(000)=1736, GOF=1.037; final R indices: R1=0.0688 [I>2σ(I)], wR2=0.2036; R indices (all data): R1=0.0801, wR2=0.2440. Salt 6: C50H72N4O7S2, CCDC #736550; M=905.26, monoclinic, a=16.2311(11), b=9.0989(7), c=36.055(3)Å, V=5308.4(7)Å3, space group C2/c, Z=4, T=298(2)K, μ (Mo-Kα)=0.148mm-1, F(000)=1912, GOF=1.0649; final R indices: R1=0.0659 [I>2σ(I)], wR2=0.2168; R indices (all data): R1=0.0822, wR2=0.2332. The crystallographic data for the complexes have been deposited with the Cambridge Crystallographic Data Centre. Copies of this information may be obtained free of charge from the Director, CCDC, 12 Union Road, Cambridge, CB2 1EZ, UK (fax: +44 1223 336033, e-mail: or ). http://www.ccdc.cam.ac.uk/.