An intramolecular charge transfer fluorescent probe: Synthesis, structure and selective fluorescent sensing of Cu +2

Journal of Fluorescence

Volumn 21, Issue 4, 2011, Pages 1813-1823

  Jayabharathi, Jayaraman ^a   Thanikachalam, Venugopal ^a   Srinivasan, Natesan ^a   Jayamorthy, Karunamoorthy ^a   Perumal, Marimuthu Venkatesh ^a  

^a ANNAMALAI UNIVERSITY   (India)

Author keywords

CIS; ESIPT; NMR; PES; X ray

Indexed keywords

AMMONIUM ACETATE; AROMATIC ALDEHYDE; CHN ANALYSIS; CIS; DFT CALCULATION; ESIPT; EXCITED-STATE INTRAMOLECULAR PROTON TRANSFER; FLUORESCENT PROBES; FLUORESCENT SENSING; GOOD YIELD; IMIDAZOLE DERIVATIVES; INTERCONVERSIONS; INTRA-MOLECULAR CHARGE TRANSFER; MOLECULAR IODINE; NMR SPECTRUM; PES; ROTAMERS; SHORT REACTION TIME; SOLVENT FREE CONDITIONS;

ALDEHYDES; AMMONIUM COMPOUNDS; CHARGE TRANSFER; EMISSION SPECTROSCOPY; FLUORESCENCE; GROUND STATE; IODINE; ION EXCHANGE; KETONES; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; ORGANIC POLYMERS; PLANTS (BOTANY); SYNTHESIS (CHEMICAL);

EXCITED STATES;

COPPER; FLUORESCENT DYE; IMIDAZOLE DERIVATIVE;

ARTICLE; CHEMISTRY; FLUORESCENCE; QUANTUM THEORY; SYNTHESIS;

COPPER; FLUORESCENCE; FLUORESCENT DYES; IMIDAZOLES; QUANTUM THEORY;

EID: 80053385286     PISSN: 10530509     EISSN: None     Source Type: Journal    
DOI: 10.1007/s10895-011-0876-5     Document Type: Article

References (24)

1. Qian Y, Li S, Zhang G, Wang Q, Wang S, Xu H, Li C, Li Y, Yang G (2007) Aggregation-induced emission enhancement of 2-(2'-Hydroxyphenyl)benzothiazole- based excited-state intramolecular proton-transfer compounds. J Phys Chem A 111:5861-5868 (Pubitemid 46918216)
2. Rodembusch FS, Leusin FP, Campo LF, Stefani V (2007) Excited state intramolecular proton transfer in amino 2-(2'-hydroxyphenyl) benzazole derivatives: effects of the solvent and the amino group position. J Lumin 126:728-734 (Pubitemid 46778863)
3. Wu Y, Peng X, Fan J, Gao S, Tian M, Zhao J, Sun S (2007) Fluorescence sensing of anions based on inhibition of excitedstate intramolecular proton transfer. J Org Chem 72:62-66
4. Das K, Sarkar N, Ghosh AK,Majumdar D, Nath DN, Bhattacharyya K (1994) Excited state intramolecular proton transfer in 2-(2'- hydroxyphenyl) benzimidazole and -benzoxazole: effect of rotamerism and hydrogen-bonding. J Phys Chem 98:9126-9132
5. Lambardino JG, Wiseman EH (1974) Preparation and antiinflammatory activity of some nonacidic trisubstituted imidazoles. J Med Chem 17:1182-1188
6. Maier T, Schmierer R, Bauer K, Bieringer H, Buerstell H, Sachse B (1989) US Patent 820335, 1989. Chem Abstr 111:19494
7. Lantos I, Zhang W, Shiu X, Eggleston DS (1993) Synthesis of imidazoles via hetero-cope rearrangements. J Org Chem 58:7092-7095 (Pubitemid 24015775)
8. Parveen A, AhmedMD, Shaikh KA, Deshmukh SP, Pawar RP (2007) Efficient synthesis of 2,4,5-triaryl substituted imidazoles under solvent free conditions at room temperature. Arkivoc xvi:12-18
9. Jianwei S, Dong Y, Cao L, Wang X, Wang S, Hu YY (2004) Highly efficient chemoselective deprotection of O, O-Acetals and O, O-Ketals catalyzed by molecular iodine in acetone. J Org Chem 69:8932-8934 (Pubitemid 39603057)
10. Frisch MJ, Trucks GW, Schlegel HB, Scuseria GE, Robb MA, Cheeseman JR, Montgomery JA, Vreven T Jr, Kudin KN, Burant JC, Millam JM, Iyengar SS, Tomasi J, Barone V, Mennucci B, Cossi M, Scalmani G, Rega N, Petersson GA, Nakatsuji H, Hada M, Ehara M, Toyota K, Fukuda R, Hasegawa J, Ishida M, Nakajima T, Honda Y, Kitao O, Nakai H, Klene M, Li X, Knox JE, Hratchian P, Cross JB, Adamo C, Jaramillo J, Gomperts R, Stratmann RE, Yazyev O, Austin AJ, Cammi R, Pomelli C, Ochterski JW, Ayala PY, Morokuma K, Voth GA, Salvador P, Dannenberg JJ, Zakrzewski VG, Dapprich S, Daniels AD, Strain MC, Farkas O, Malick DK, Rabuck AD, Raghavachari K, Foresman JB, Ortiz JV, Cui Q, Baboul AG, Clifford S, Cioslowski J, Stefanov BB, Liu G, Liashenko A, Piskorz P, Komaromi I, Martin RL, Fox DJ, Keith T, Al-Laham MA, Peng CY, Nanayakkara A, Challacombe M, Gill PMW, Johnson B, Chen W, Wong MW, Gonzalez C, Pople JA (2004) Gaussian 03, Revision C.02, Gaussian, Inc.: Wallingford, CT
11. Saravanan K, Srinivasan N, Thanikachalam V, Jayabharathi J (2011) Synthesis and photophysics of some novel imidazole derivatives used as sensitive fluorescent chemisensors. J Fluoresc 21:65-80
12. Jayabharathi J, Thanikachalam V, Srinivasan N, Saravanan K (2010) Synthesis, structure, luminescent and Intramolecular proton transfer in some imidazole derivatives. J Fluoresc. doi:10.1007/s10895-010-0747-5
13. Barbara PF, Walsh PK, Brus LE (1989) Picosecond kinetic and vibrationally resolved spectroscopic studies of intramolecular excited-state hydrogen atom transfer. J Phys Chem 93:29-34
14. Feng K, Hsu FL, Veer DVD, Bota K, Bu XR (2004) Tuning fluorescence properties of imidazole derivatives with thiophene and thiazole. J Photochem Photobiol A Chem 165:223-228
15. Woolfe GJ, Melzig M, Schneider S, Dörr F (1983) The role of tautomeric and rotameric species in the photophysics of 2-(2'- hydroxyphenyl) benzoxazole. Chem Phys 77:213-221
16. Sobolewski AL (1993) The mechanism of excited-state hydrogen transfer in 2-hydroxypyridine. Chem Phys Lett 211:293-299
17. Dogra SK (2005) Excited-state inter- and intramolecular proton transfer inmethyl 3-hydroxy-2-quinoxalinate: effects of solvent and acid or base concentrations. J Lumin 114:101-117 (Pubitemid 40952652)
18. Zhou Z, Fahrni CJ (2004) A fluorogenic probe for the copper(I)- catalyzed azide-alkyne ligation reaction: modulation of the fluorescence emission via 3(n, π*) 1(π, π*) inversion. J Am Chem Soc 126:8862-8863 (Pubitemid 38971037)
19. Huang WS, Lin JT, Chien CH, Tao YT, Sun SS, Wen YS (2004) Highly phosphorescent Bis-cyclometalated Iridium complexes containing Benzimidazole-Based ligands. Chem Mater 16:2480-2488
20. Chen CH, Shi J (1998) Metal chelates as emitting materials for organic electroluminescence. Coord Chem Rev 171:161-174
21. Fleming I (1976) Frontier orbitals and organic chemical reactions. Wiley, NewYork, p 5
22. Padmaja L, Ravikumar C, Sajan D, Hubert Joe I, Jayakumar VS, Pettit GR, Faurskov Neilsen O (2009) Density functional study on the structural conformations and intramolecular charge transfer from the vibrational spectra of the anticancer drug combretastatin- A2. J Raman Spectrosc 40:419-428
23. Ravikumar C, Hubert Joe I, Jayakumar VS (2008) Charge transfer interactions and nonlinear optical properties of push-pull chromophore benzaldehyde phenylhydrazone: a vibrational approach. Chem Phys Lett 460:552-558
24. FukuiK,Yonezawa T, Shingu H (1952)Amolecular orbital theory of reactivity in aromatic hydrocarbons. J Chem Phys 20:722-725