Synthesis and Photophysical Characteristics of a Novel Two-photon Absorption Unsymmetrical Ketocoumarin

doi:10.7517/j.issn.1674-0475.2006.03.187

Abstract

Abstract: A novel ketocoumarin derivative C3 presented a Dπ₁-A-π₂-D structure with diethylamino as the electron donor(D),carbonyl as the electron acceptor(A),coumarin and stilbene as the conjugating bridge was synthesized.Its photophysical characteristics were studied using UV-Vis and fluorescence spectra.The result showed that upon excitation compound C3 could form its intramolecular charge transfer state easily and furthermore transform to a twisted intramolecular charge transfer state accompanying with a very large change of dipole moment.The two-photon absorption cross-section of the new compound was measured by the up-converted fluorescence method with femtosecond laser pulses.It was obtained as 1292 GM at 850 nm,which is one to two orders of magnitudes larger than those of the reference compounds C1 and C2.

Key words: ketocoumarin, stilbene, intramolecular charge transfer, two-photon absorption

CLC Number:

LI Xue, WANG Tao, ZHAO Yu-xia, WU Fei-peng. Synthesis and Photophysical Characteristics of a Novel Two-photon Absorption Unsymmetrical Ketocoumarin[J]. Imaging Science and Photochemistry, 2006, 24(3): 187-196.

References

[1] Kawata S,Sun H -B,Tanaka T,Takada K.Finer features for functional microdevices[J].Nature,2001,412:697-698.
[2] Parthenopoulos D A,Rentzepis P M.Three-dimensional optical storage memory[J].Science,1989,245:843-845.
[3] Denk W,Strickler J H,Webb WW.Two-photon laser scanning fluorescence microscopy[J].Science,1990,248:73-76.
[4] He G S,Xu G C,Prasad P N,Reinhardt B A,Bhatt J C,Dillard A G.Two-photon absorption and optical-limiting properties of novel organic compounds[J].Opt.Lett.,1995,20:435-437.
[5] BhawalkarJ E,Kumar ND,ZhaoCF,ParsadP N.Two-photon photodynamic therapy[J].J.Clin.LaserMed.Surg.,1997,15:201-204.
[6] (a) Albota M,Beljonne D,Brédas J L,et al.Design of organic molecules with large two-photon absorption cross sections[J].Science,1998,281:1653-1656.(b) Ventelon L,Charier S,Moreaux L,Mertz J,Blanchard-Desce M.Nanoscale push-push dihydrophenanthrene derivatives as novel fluorophores for two-photon-excited fluorescence[J].Angew.Chem.Int.Ed.,2001,40:2098-2101.(c) Chung S J,Kim K S,Lin T C,He G S,Swiatkiewicz J,Prasad P N.Cooperative enhancement of two-photon absorption in multi-branched structures[J].J.Phys.Chem.B,1999,103:10741-10745.
[7] 王涛,吴飞鹏,施盟泉,高放,杨永源.一种新型香豆素酮可见光敏化染料的合成及其光引发性质的研究[J].化学学报,2004,62:527-531.Wang T,Wu F P,Shi M Q,Gao F,Yang Y Y.Synthesis of a novel ketocoumarin visible-light photosensitive dye and its initiating properties[J].Acta Chim.Sinica,2004,62:527-531.
[8] Bredereck H,Simchen G,Griebenow W.Synthese und reaktionen von[α-(dimethylaminomethylen)-benzyltriphenylphosphonium-Salzen[J].Chem.Ber.,973,106:3732-3745.
[9] Demas J N,Crosby G A.The measurement of photoluminescence quantum yields.A review[J].J.Phys.Chem.,1971,75:991-1024.
[10] Xu C,Webb W W.Measurement of two-photon excitation cross-sections of molecular fluorophores with data from690 to 1050 nm[J].J.Opt.Soc.Am.B,1996,13:481-491.
[11] López Arbeloa T,López Arbeloa F,José Tapia M,Lopez Arbeloa I.Hydrogen-bonding effect on the photophysical properties of 7-aminocoumarin derivatives[J].J.Phy.Chem.,1993,97:4704-4707.
[12] Bilot L,Kawski A.Zur theorie des einflüsses von losungsmitteln auf die elektronenspektren der moleküle[J].Z.Naturforsch Teil A,1962,17:621-627.
[13] Gao F,Li H R,Yang Y Y.Influence of the molecular structure and medium on the absorption and emission character of ketocoumarin derivatives and probability of as fluorescence probes[J].Dyes and Pigments,2000,47:231-238.
[14] Nag A,Chakrabarty T,Bhattacharyya K.Effect of.gamma.-cyclodextrin on the intramolecular charge transfer processes in aminocoumarin laser dyes[J].J.Phys.Chem.,1990,94:4203-4206.

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