Browse > Article
http://dx.doi.org/10.5012/jkcs.2014.58.3.297

The Synthesis and Light Absorption Behaviour of Novel Coumarin Chromophores  

An, Kyoung Lyong (Interface Chemistry & Engineering Research Team, Korea Research Institute of Chemical Technology)
Shin, Seung Rim (Interface Chemistry & Engineering Research Team, Korea Research Institute of Chemical Technology)
Jun, Kun (Interface Chemistry & Engineering Research Team, Korea Research Institute of Chemical Technology)
Park, Soo Youl (Interface Chemistry & Engineering Research Team, Korea Research Institute of Chemical Technology)
Publication Information
Journal of the Korean Chemical Society / v.58, no.3, 2014 , pp. 297-302 More about this Journal
Abstract
The synthetic route to coumarin systems is well established and one approach of particular interest leads to the intermediate 7-diethylamino-3-formylcoumarin. A combination of the N,N-diethylamino-coumarin donor with a wide range of acceptor groups of varying electron withdrawing strength should permit the synthesis of a series of extended coumarin dyes with absorption maxima range from 500 to 600 nm, or even beyond. In this communication, a novel efficient synthesis of indoles, benzothiazole and benzoxazole based on coumarin chromophores were achieved and the coloristic and fluorophoric properties of these chromophores were studied.
Keywords
Coumarin; Knoevenagel condensation; Fluorescence; Chromophores;
Citations & Related Records
연도 인용수 순위
  • Reference
1 Prasanna de Silva, A.; Gunaratante, H. Q. N.; Gunnlaugsson, Th.; Huxley, A. J. M.; Mc Coy, C. P.; Rademacher, J. T.; Rice, T. E. Signaling Recognition Events with Fluorescent Sensors and Switches. Chem. Rev. 1997, 97, 1515-1566.   DOI   ScienceOn
2 Prasanna de Silva, A.; Vance, T. P.; West, M. E. S.; Wright, G. D. Bright Molecules with Sense, Logic, Numeracy and Utility. Org. Biomol. Chem. 2008, 6, 2468-2481.   DOI
3 Ohkawa, M.; Ishii, K. U.S. Patent 3,933,847, 1976.
4 Horst, H. U.S. Patent 3,985,763, 1976.
5 Loew, P.; Schwander, H.; Kristinsson, H. U.S. Patent 4,064,136, 1977.
6 Loew, P. U.S. Patent 4,146,712, 1979.
7 Ayyangar, N. R.; Srinivasan, K. V.; Daniel, T. Polycyclic Compounds Part VI: Structural Features of C.I. Disperse Yellow 232. Dyes and Pigments 1990, 13(4), 301-310.   DOI
8 Ayyangar, N. R.; Snnivasan, K. V.; Daniel, T. Polycyclic Compounds Part VII: Synthesis, Laser Characteristics and Dyeing Behaviour of 7-Diethylamno-2H-1-benzopyran-2-ones. Dyes and Pigments 1991, 16(3), 197-204.   DOI
9 Moeckli, P. Preparation of Some New Red Fluorescent 4-Cyanocoumarin Dyes. Dyes and Pigments 1980, 1(1), 3-15.   DOI
10 Mockli, P. U.S. Patent 4,609,738, 1986
11 Mockli, P. U.S. Patent 5,547,579, 1985.
12 Mach, W.; Augart, D.; Scheuermann, H. Ger. Offen. 2,253,538,1972.
13 Horng, M. L.; Gardeski, J. A.; Papazyan, A.; Maroncelli,M. Subpicosecond Measurement of Polar Salvation Dynamics:Coumarin 153 Revisited. J. Phys. Chem. 1995, 99, 17311-17337.   DOI
14 Arbeloa, T. L.; Arbeloa, F. L.; Arbeloa, I. L. Influence ofFluorinated Group on the Photophysics of 7-Aminocoumarins.J. Luminescence 1996, 68, 149-155.   DOI
15 Du, D. M.; Wang, Y. M.; Meng, J. B. Micro-environmentalEffects on the Photochemical and Photophysical Processesof Long Chain Coumarin Esters. Chem. J. Chin. Univ.-Chin.1998, 19, 1611-1613.
16 Raju, B. B.; Costa, S. M. B. Photophysical Properties of7-Diethylaminocoumarin Dyes in Dioxanewater Mixtures:Hydrogen Bonding, Dielectric Enrichment and PolarityEffects. Phys. Chem. Chem. Phys. 1999, 1, 3539-3547.   DOI
17 Ramalingam, A.; Sivaram. B. M.; Palamisamy, P. K.; Masilamani,V. Photophysics of TICT States of 7-Diethylamino-4-methyl Coumarin Dye by Energy Transfer Techniques. Spectrochim.Acta, Part A: Molec. Biomolec. Spect. 2000, 56,1205-1210.   DOI
18 Raikar, U. S.; Renuka, C. G.; Nadaf, Y. F.; Mulimanim B.G.; Karguppikar, A. M.; Soudagar, M. K. Solvent Effectson the Absorption and Fluorescence Spectra of Coumarins6 and 7 Molecules: Determination of Ground State and ExcitedState Dipole Moment. Spectrochim. Acta. 2006, Part A65, 673-677.   DOI
19 Mandal, P. K.; Paul, A.; Samanta, A. Fluorescence Studiesof Environmentally Benign Solvents: Solvation Dynamics of Coumarin 102 in [BMIM][BF4]. Res. Chem. Intermed. 2005,31, 575-583.   DOI
20 Raikar, U. S.; Renuka, C. G.; Nadaf, Y. F.; Mulimani, B.G.; Karguppikar, A. M. Rotational Diffusion and SolvatochromicCorrelation of Coumarin 6 Laser Dye. J. Fluorescence2006, 16, 847-854..   DOI
21 Tablet, C.; Hildebrand, M. Quenching of the Fluorescenceof Carboxy-5,6-benzocoumarin by Aromatic Amines. J. Photochem.Photobiol. A Chem. 2007, 189, 73-79.   DOI
22 Wang, T.; Zhao, Y.; Shi, M.; Wu, F. The Synthesis of NovelCoumarin Dyes and the Study of Their PhotoreactionProperties. Dyes Pigments 2007, 75, 104-110.   DOI
23 Hantzsch, A. Ber. Dtsch, Chem. Ges, 1922, 55, 953.
24 Pugzlys, A.; Hania, P. R.; Augulis, R.; Duppen, S. K.;Van Loosdrecht, P. H. M. Int. J. Photoenergy 2006, 24-29.
25 Camposeo, A.; Persano, L.; Del Carro, P.; Cirgili, T.; Cingolani,R.; Pisignano, D. Org. Electro 2007, 8, 114-119.   DOI
26 Ricceri, R.; Abbotto, A.; Facchetti, A.; Pagani, G. A.; Gabrielli, G. Langmuir 1997, 13, 3434-3441.   DOI