NLOphoric Red Emitting Bis Coumarins with O-BF2-O core - Synthesis, Photophysical Properties and DFT Studies
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- 作者：Abhinav B. Tathe ; Nagaiyan Sekar
- 关键词：Bis ; coumarin ; Chalcone ; DFT ; TD ; DFT ; Red emitting dyes ; NLO properties
- 刊名：Journal of Fluorescence
- 出版年：2016
- 出版时间：March 2016
- 年：2016
- 卷：26
- 期：2
- 页码：471-486
- 全文大小：1,652 KB
- 参考文献：1.Liu X, Cole JM, Waddell PG et al (2012) Molecular origins of optoelectronic properties in coumarin dyes: toward designer solar cell and laser applications. J Phys Chem A 116:727–737. doi:10.1021/jp209925y CrossRef PubMed
2.Mir FA (2015) Optical and Schottky diode performance of Au/4-hydroxy Coumarin/ITO heterojunction. Opt - Int J Light Electron Opt 126:24–27. doi:10.1016/j.ijleo.2014.07.146 CrossRef
3.Kumar S, Singh P, Srivastava R et al (2014) Engineering fused coumarin dyes: a molecular level understanding of aggregation quenching and tuning electroluminescence via alkyl chain substitution. J Mater Chem C 2:6637. doi:10.1039/C4TC00807C CrossRef
4.Huang L, Chen Y, Liang B et al (2014) A furanyl acryl conjugated coumarin as an efficient inhibitor and a highly selective off–on fluorescent probe for covalent labelling of thioredoxin reductase. Chem Commun 50:6987. doi:10.1039/c4cc02119c CrossRef
5.Signore G, Nifosì R, Albertazzi L et al (2010) Polarity-sensitive coumarins tailored to live cell imaging. J Am Chem Soc 132:1276–1288. doi:10.1021/ja9050444 CrossRef PubMed
6.Cigáň M, Donovalová J, Szöcs V et al (2013) 7-(Dimethylamino)coumarin-3-carbaldehyde and its phenylsemicarbazone: TICT excited state modulation, fluorescent H-aggregates, and preferential solvation. J Phys Chem A 117:4870–4883. doi:10.1021/jp402627a PubMed
7.Keskin SS, Aslan N, Bayrakçeken F (2009) Optical properties and chemical behavior of Laser-dye Coumarin-500 and the influence of atmospheric corona discharges. Spectrochim Acta A Mol Biomol Spectrosc 72:254–259. doi:10.1016/j.saa.2008.09.024 CrossRef PubMed
8.Chen J, Liu W, Ma J et al (2012) Synthesis and properties of fluorescence dyes: tetracyclic pyrazolo[3,4-b]pyridine-based coumarin chromophores with intramolecular charge transfer character. J Org Chem 77:3475–3482. doi:10.1021/jo3002722 CrossRef PubMed
9.Krzeszewski M, Vakuliuk O, Gryko DT (2013) Color-tunable fluorescent dyes based on benzo[c]coumarin. Eur J Org Chem 5631–5644. doi: 10.1002/ejoc.201300374
10.Hong G, Lee JC, Robinson JT et al (2012) Multifunctional in vivo vascular imaging using near-infrared II fluorescence. Nat Med 18:1841–1846. doi:10.1038/nm.2995 CrossRef PubMed PubMedCentral
11.Behnke T, Mathejczyk JE, Brehm R et al (2013) Target-specific nanoparticles containing a broad band emissive NIR dye for the sensitive detection and characterization of tumor development. Biomaterials 34:160–170CrossRef PubMed
12.Sotgiu G, Galeotti M, Samorí C et al (2011) Push-pull amino succinimidyl ester thiophene-based fluorescent dyes: synthesis and optical characterization. Chemistry 17:7947–7952. doi:10.1002/chem.201100142 CrossRef PubMed
13.Alexander VM, Sano K, Yu Z et al (2012) Galactosyl human serum albumin-NMP1 conjugate: a near infrared (NIR)-activatable fluorescence imaging agent to detect peritoneal ovarian cancer metastases. Bioconjug Chem 23:1671–1679. doi:10.1021/bc3002419 CrossRef PubMed PubMedCentral
14.Kolmakov K, Wurm CA, Meineke DNH et al (2014) Polar red-emitting rhodamine dyes with reactive groups: synthesis, photophysical properties, and two-color STED nanoscopy applications. Chemistry 20:146–157. doi:10.1002/chem.201303433 CrossRef PubMed
15.Kolmakov K, Wurm C, Sednev MV et al (2012) Masked red-emitting carbopyronine dyes with photosensitive 2-diazo-1-indanone caging group. Photochem Photobiol Sci 11:522–532. doi:10.1039/c1pp05321c CrossRef PubMed
16.Griffiths J, Millar V, Bahra G (1995) The influence of chain length and electron acceptor residues in 3-substituted 7- N, N-diethylaminocoumarin dyes. Dye Pigment 28:327–339CrossRef
17.Moeckli P (1980) Preparation of some new red fluorescent 4-cyanocoumarin dyes. Dye Pigment 1:3–15CrossRef
18.Raju BB, Varadarajan TS (1995) Spectroscopic studies of 7-diethylamino-3-styryl coumarins. J Photochem Photobiol A Chem 85:263–267. doi:10.1016/1010-6030(94)03905-A CrossRef
19.Tathe AB, Gupta VD, Sekar N (2015) Synthesis and combined experimental and computational investigations on spectroscopic and photophysical properties of red emitting 3-styryl coumarins. Dye Pigment 119:49–55. doi:10.1016/j.dyepig.2015.03.023 CrossRef
20.Huang S-T, Jian J-L, Peng H-Z et al (2010) The synthesis and optical characterization of novel iminocoumarin derivatives. Dye Pigment 86:6–14CrossRef
21.Kohn W, Sham LJ (1965) Self-consistent equations including exchange and correlation effects. Phys Rev 140:A1133–A1138. doi:10.1103/PhysRev.140.A1133 CrossRef
22.Menzel R, Ogermann D, Kupfer S et al (2012) 4-methoxy-1,3-thiazole based donor-acceptor dyes: characterization, X-ray structure, DFT calculations and test as sensitizers for DSSC. Dye Pigment 94:512–524. doi:10.1016/j.dyepig.2012.02.014 CrossRef
23.Lee C, Yang W, Parr RG (1988) Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density. Phys Rev B 37:785–789. doi:10.1103/PhysRevB.37.785 CrossRef
24.Tomasi J, Mennucci B, Cammi R (2005) Quantum mechanical continuum solvation models. Chem Rev 105:2999–3093. doi:10.1021/cr9904009 CrossRef PubMed
25.Frisch MJ, Trucks GW, Schlegel HB, et al. (2009) Gaussian 09, Revision C.01. Gaussian 09, Revis. B.01, Gaussian, Inc., Wallingford CT
26.Hamdi N, Bouabdallah F, Romerosa A, Benhassen R (2010) Expedious synthesis for α, β-unsaturated coumarin derivatives using boran chelates: a novel class of potential antibacterial and antioxidant agents. C R Chim 13:1261–1268. doi:10.1016/j.crci.2009.10.001 CrossRef
27.Razzaq T, Kappe CO (2007) Rapid preparation of pyranoquinolines using microwave dielectric heating in combination with fractional product distillation. Tetrahedron Lett 48:2513–2517. doi:10.1016/j.tetlet.2007.02.052 CrossRef
28.Manaev AV, Okhrimenko IN, Lyssenko KA, Traven’ VF (2008) Synthesis and condensation reactions of the boron difluoride complex with 3-acetyl-4-hydroxy-1-methyl-2-quinolone. Russ Chem Bull 57:1734–1739. doi:10.1007/s11172-008-0229-y CrossRef
29.Turro NJ (1978) Modern molecular photochemistry. Benjamin-Cummings, New York
30.Coe BJ, Harris JA, Asselberghs I et al (2002) Quadratic nonlinear optical properties of N-aryl stilbazolium dyes. Adv Funct Mater 12:110–116. doi:10.1002/1616-3028(20020201)12:2<110::AID-ADFM110>3.0.CO;2-Y CrossRef
31.Lippert E (1957) Spektroskopische Bestimmung des Dipolmomentes aromatischer Verbindungen im ersten angeregten Singulettzustand. Z Elektrochem, Ber Bunsenges Phys Chem 61:962–975. doi:10.1002/bbpc.19570610819
32.Valeur B (2001) Molecular Fluorescence, 2nd edn. Wiley VCH. doi:10.1002/3527600248
33.Sharafudeen KN, Adithya A, Vijayakumar S et al (2011) Multiphoton absorption process and self-focusing effect in coumarin derivative doped PMMA films by Z-scan and optical limiting studies. Curr Appl Phys 11:1089–1093. doi:10.1016/j.cap.2011.02.001 CrossRef
34.Sun YF, Wang HP, Chen ZY, Duan WZ (2013) Solid-state fluorescence emission and second-order nonlinear optical properties of coumarin-based fluorophores. J Fluoresc 23:123–130. doi:10.1007/s10895-012-1125-2 CrossRef PubMed
35.Raj RK, Gunasekaran S, Gnanasambandan T, Seshadri S (2015) Combined spectroscopic and DFT studies on 6
omo-4-chloro-3-formyl coumarin. Spectrochim Acta Part A Mol Biomol Spectrosc 139:505–514. doi:10.1016/j.saa.2014.12.024 CrossRef
36.Abbotto A, Beverina L, Bradamante S et al (2003) A distinctive example of the cooperative interplay of structure and environment in tuning of intramolecular charge transfer in second-order nonlinear optical chromophores. Chem - A Eur J 9:1991–2007. doi:10.1002/chem.200204356 CrossRef
37.Oudar JL, Zyss J (1982) Structural dependence of nonlinear-optical properties of methyl-(2,4-dinitrophenyl)-aminopropanoate crystals. Phys Rev A 26:2016–2027. doi:10.1103/PhysRevA.26.2016 CrossRef
38.Morley JO, Docherty VJ, Pugh D (1987) Non-linear optical properties of organic molecules. Part 2. Effect of conjugation length and molecular volume on the calculated hyperpolarisabilities of polyphenyls and polyenes. J Chem Soc Perkin Trans 2:1351. doi:10.1039/p29870001351 CrossRef
39.Meshulam G, Kotler Z, Berkovic G (2002) Time-resolved electric-field-induced second harmonic: simultaneous measurement of first and second molecular hyperpolarizabilities. Opt Lett 27:1132–1134. doi:10.1364/OL.27.001132 CrossRef PubMed
40.Heesink GJT, Ruiter AGT, Van Hulst NF, Bölger B (1993) Determination of hyperpolarizability tensor components by depolarized hyper Rayleigh scattering. Phys Rev Lett 71:999–1002. doi:10.1103/PhysRevLett.71.999 CrossRef PubMed
41.Oudar JL, Chemla DS (1977) Hyperpolarizabilities of the nitroanilines and their relations to the excited state dipole moment. J Chem Phys 66:2664. doi:10.1063/1.434213 CrossRef
42.Carlotti B, Flamini R, Kikaš I et al (2012) Intramolecular charge transfer, solvatochromism and hyperpolarizability of compounds bearing ethenylene or ethynylene bridges. Chem Phys 407:9–19. doi:10.1016/j.chemphys.2012.08.006 CrossRef
43.Paley MS, Harris JM, Looser H et al (1989) A solvatochromic method for determining second-order polarizabilities of organic molecules. J Org Chem 54:3774–3778. doi:10.1021/jo00277a007 CrossRef
44.McRae EG (1957) Theory of solvent effects on molecular electronic spectra. Frequency Shifts. J Phys Chem 61:562–572. doi:10.1021/j150551a012 CrossRef
45.Bruni S, Cariati E, Cariati F et al (2001) Determination of the quadratic hyperpolarizability of trans-4-[4-(dimethylamino)styryl]pyridine and 5-dimethylamino-1,10-phenanthroline from solvatochromism of absorption and fluorescence spectra: A comparison with the electric-field-induced second-harmon. Spectrochim Acta - Part A Mol Biomol Spectrosc 57:1417–1426. doi:10.1016/S1386-1425(00)00483-2 CrossRef
46.Oudar JL (1977) Optical nonlinearities of conjugated molecules. Stilbene derivatives and highly polar aromatic compounds. J Chem Phys 67:446. doi:10.1063/1.434888 CrossRef
47.De Paris R (1982) Nonlinear-optical properties. Phys Rev A 26:2016–2027CrossRef
48.Kwon OP, Jazbinsek M, Seo JI et al (2010) First hyperpolarizability orientation in asymmetric pyrrole-based polyene chromophores. Dye Pigment 85:162–170. doi:10.1016/j.dyepig.2009.10.019 CrossRef
49.Weaver CS, Smith SW, Hyndman RD et al (1991) + 0.028. Science 252:103–106CrossRef
50.Cheng L-T, Tam W, Stevenson SH et al (1991) Experimental investigations of organic molecular nonlinear optical polarizabilities. 1. Methods and results on benzene and stilbene derivatives. J Phys Chem 95:10631–10643. doi:10.1021/j100179a026 CrossRef
51.Dirk CW, Cheng L-T, Kuzyk MG (1992) A simplified three-level model describing the molecular third-order nonlinear optical susceptibility. Int J Quantum Chem 43:27–36. doi:10.1002/qua.560430106 CrossRef
52.Kuzyk MG, Dirk CW (1990) Effects of centrosymmetry on the nonresonant electronic third-order nonlinear optical susceptibility. Phys Rev A 41:5098–5109. doi:10.1103/PhysRevA.41.5098 CrossRef PubMed - 作者单位：Abhinav B. Tathe (1)
Nagaiyan Sekar (1)
1. Tinctorial Chemistry Group, Department of Dyestuff Technology, Institute of Chemical Technology, N. P. Marg, Matunga, Mumbai, MH, India, 400019 - 刊物类别：Biomedical and Life Sciences
- 刊物主题：Biomedicine
Biomedicine
Biophysics and Biomedical Physics
Biotechnology
Biochemistry
Analytical Chemistry - 出版者：Springer Netherlands
- ISSN：1573-4994
文摘
The red emitting dyes were synthesized by employing coumarin core as a donor and boron-bonded coumarin as an acceptor. 7-(N,N-Diethylamino)-coumarin 3-aldehyde was reacted with 3-acetyl-4-hydroxy-coumarin, 7-(N,N-diethylamino)-3-acetyl-4-hydroxy-coumarin and 3-acetyl-4-hydroxy-1-methyl-quinolone to form the corresponding chalcones. The synthesized chalcones were though red shifted as compared to the parent coumarin, and were not emitting in red region. The BF2-complexation was used as a tool to introduce a red shift in the molecules. The BF2-complexes synthesized were found to be red emitting and show higher one photon absorption cross section. The solvatochromism shown by these dyes was studied in the light of solvent polarity parameters. DFT calculations were used to understand the photophysical properties of the synthesized dyes. NLO properties of the dyes were estimated by solvatochromic and computational methods. All the molecules synthesized were characterised with the HRMS and NMR spectral Analysis.