Charge transfer in 1,8-naphthalimide: A combined theoretical and experimental approach

Photochemistry and Photobiology

Volumn 86, Issue 1, 2010, Pages 47-54

  Manna, Anamika ^a   Chakravorti, Sankar ^a  

^a DEPARTMENT OF MATERIALS SCIENCE   (India)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 73649096547     PISSN: 00318655     EISSN: None     Source Type: Journal    
DOI: 10.1111/j.1751-1097.2009.00625.x     Document Type: Article

References (35)

1. Gan, J., K. Chen, C. P. Chang H. Tian (2003) Luminescent properties and photo-induced electron transfer of naphthalimides with piperazine substituent. Dyes Pigm. 57, 21 28.
2. De Silva, A., B. Mc Caughan, B. Mckinney M. Querol (2003) Newer optical-based molecular devices from older coordination chemistry. Dalton Trans. 10, 1902 1913.
3. De Silva, A., A. Goligher, H. Gunaratne T. Rice (2003) The pH-dependent fluorescence of pyridylmethyl-4-amino-1,8-naphthalimides. ARKIVOC 7, 229 243.
4. Patrick, L. A. Whiting (2002) Synthesis of some polymerisable fluorescent dyes. Dyes Pigm. 55, 123 132.
5. Martin, E., R. Weigand A. Pardo (1996) Solvent dependence of the inhibition of intramolecular charge-transfer in N-substituted 1,8-naphthalimide derivatives as dye lasers. J. Lumin. 68, 157 164.
6. Tao, Z. F. X. Qian (1999) Naphthalimide hydroperoxides as photonucleases: Substituent effects and structural basis. Dyes Pigm. 43, 139 145.
7. Stewart, W. (1981) Synthesis of 3,6-disulfonated 4-aminonaphthalimides. J. Am. Chem. Soc. 103, 7615 7620.
8. Correa, M. M. R., V. C. Filho, I. Grabchev V. Bojinov (2002) 4-Nitro-1,8-naphthalimides exhibit antinociceptive properties. Pharmazie 56, 430 431.
9. Zhu, W., C. Hu, K. Chen H. Tian (1998) Luminescent properties of copolymeric dyad compounds containing 1,8-naphthalimide and 1,3,4-oxadiazole. Synth. Met. 96, 151 154.
10. Grabchev, I., J. M. Chovelon X. Qian (2003) A polyamidoamine dendrimer with peripheral 1,8-naphthalimide groups capable of acting as a PET fluorescent sensor for metal cations. New J. Chem. 27, 337 340.
11. + in neutral aqueous solution: 4,5-Diaminoalkeneamino-N-alkyl-l,8-naphthalimides. Tetrahedron Lett. 45, 3969 3973.
12. Cacialli, F., R. Friend, C. Bouche, P. Le Barny, H. Facoetti, F. Soyer P. Robin (1998) Naphthalimide side-chain polymers for organic light-emitting diodes: Band-offset engineering and role of polymer thickness. J. Appl. Phys. 83 (4 2343 2356.
13. Grabchev, I., I. Moneva, V. Bojinov S. Guittonneau (2000) Synthesis and properties of fluorescent 1,8-naphthalimide dyes for application in liquid crystal displays. J. Mater. Chem. 10, 1291 1296.
14. Cosnard, F. V. Wintgens (1998) A new fluoroionophore derived from 4-amino-N-methyl-1,8-naphthalimide. Tetrahedron Lett. 39, 2751 2754.
15. Pardo, A., J. M. L. Poyato, E. Martin, J. J. Camacho, D. Reyman, M. F. Brana J. M. Castelano (1989) Solvent effects on the photophysical properties of N-substituted 1,8-naphthalimide derivatives. J. Photochem. Photobiol. A, Chem. 46, 323 328.
16. Magalhães, J. L., R. V. Pereira, E. R. Triboni, P. Berci Filho, M. H. Gehlen F. C. Nart (2006) Solvent effect on the photophysical properties of 4-phenoxy-N-methyl-1,8-naphthalimide. J. Photochem. Photobiol. A, Chem. 183, 165 170.
17. Wintgens, V., P. Valat, J. Kossanyi, L. Biczok, A. Demeter T. Bérces (1994) Spectroscopic properties of aromatic dicarboximides. Part 1. -N-H and N-methyl-substituted naphthalimides. J. Chem. Soc., Faraday Trans. 90, 411 421.
18. Moodie, R. B., A. J. Sanderson R. Willmer (1990) Electrophilic aromatic substitution. Part 36. Kinetics of aromatic nitrations in solutions of dinitrogen pentaoxide and of nitronium salts in nitric acid. J. Chem. Soc., Perkin Trans. 2, 837 842.
19. Hayashi, H., S. Nagakura, Y. Kubo K. Maruyama (1980) Mechanistic studies of photochemical reactions of N-ethylphthalmide with olefins. Chem. Phys. Lett 72, 291 294.
20. Sahoo, D., T. Adhikary, P. Chowdhury, S. C. Roy S. Chakravorti (2008) Understanding the photophysics of 4-nitro-1-hydroxy-2-naphthoic acid: A controlled excited state proton transfer. Chem. Phys. 352, 175 184.
21. Crosby, G. A. J. M. Demas (1971) Measurement of photoluminescence quantum yields. J. Phys. Chem. 75 (8 991 1024.
22. Foresman, J. B., M. Head-Gordon, J. A. Pople M. J. Frisch (1992) Toward a systematic molecular orbital theory for excited states. J. Phys. Chem. 96, 135 149.
23. Jacquemin, D., E. A. Perpète, G. Scalmani, M. J. Frisch, I. Ciofini C. Adamo (2007) Fluorescence of 1,8-naphthalimide: A PCM-TD-DFT investigation. Chem. Phys. Lett. 448, 3 6.
24. Yin, S., H. Xu, W. Shi, Y. Gao, Y. Song B. Z. Tang (2006) The enhancement effect of hydrogen bond on the third-order nonlinear optical properties. Dyes Pigm. 71, 138e44.
25. Tonge, P. J., R. Fausto P. R. Carey (1996) FT-IR studies of hydrogen bonding between a,b-unsaturated esters and alcohols. J. Mol. Struct. 379, 135e42.
26. Martin, E., J. L. Gu. Coronado, J. J. Camacho A. Pardo (2005) Experimental and theoretical study of the intramolecular charge transfer on the derivatives 4-methoxy and 4-acetamide 1,8-naphthalimide N-substituted. J. Photochem. Photobiol. A, Chem. 175, 1 7.
27. Samanta, A., B. Ramachandram G. Saroja (1996) An investigation of the triplet state properties of 1,8-naphthalimide: A laser flash photolysis study. J. Photochem. Photobiol. A, Chem. 101, 29 32.
28. Mahanta, S., R. B. Singh, S. Kar N. Guchhait (2008) Photoinduced intramolecular charge transfer in methyl ester of N,N′- dimethylaminonaphthyl-(acrylic)-acid: Spectroscopic measurement and quantum chemical calculations. J. Photochem. Photobiol. A, Chem. 194, 318 326.
29. Reichardt, C. (1994) Solvatochromic dyes as solvent polarity indicators. Chem. Rev. 94, 2319 2358.
30. Edward, J. T. (1970) Molecular volumes and the Stokes-Einstein equation. J. Chem. Educ. 47, 261 269.
31. Saha, S. A. Samanta (2002) Influence of the structure of the amino group and polarity of the medium on the photophysical behavior of 4-amino-1,8- naphthalimide derivatives. J. Phys. Chem. A. 106, 4763 4771.
32. Chakraborty, A., S. Kar N. Guchhait (2006) Secondary amino group as charge donor for the excited state intramolecular charge transfer reaction in trans-3-(4-monomethylamino-phenyl)-acrylic acid: Spectroscopic measurement and theoretical calculations. J. Photochem. Photobiol. A, Chem. 181, 246 256.
33. Chakraborty, A., S. Kar N. Guchhait (2006) Photophysical properties of trans-3-(4-monomethylamino-phenyl)-acrylonitrile: Evidence of twisted intramolecular charge transfer (TICT) process. Chem. Phys. 324, 733 741.
34. Chakraborty, A., S. Kar, D. N. Nath N. Guchhait (2007) Photoinduced intramolecular charge-transfer reactions in 4-amino-3-methyl benzoic acid methyl ester: A fluorescence study in condensed-phase and jet-cooled molecular beams. J. Chem. Sci. 119, 195 204.
35. Chakraborty, A., S. Kar N. Guchhait (2006) Photoinduced intramolecular charge transfer reaction in (E)-3-(4-methylamino-phenyl)-acrylic acid methyl ester: A fluorescence study in combination with TDDFT calculation. J. Phys. Chem. A. 110, 12089 12095.