Abstract
Two triphenylamine-based derivatives that can be used as two-photon absorption chromophore, tris{4-[4-(3-trifluoromethyl-3-oxopanoyl)]phenyl}amine (1) and tris{4-[4-(3-phenyl-3-oxopanoyl)] phenyl} amine (2) were successfully synthesized and fully characterized by elemental analysis, IR, 1H NMR and MS. The single crystal X-ray diffraction analysis showed that the molecules possess D-(π-A)3 structures. One-and two-photon absorption and fluorescence in various solvents were experimentally investigated. A data recording experiment proved the potential application of these chromophores.
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Marder S R. Organic nonlinear optical materials: Where we have been and where we are going. Chem Commun, 2006, 131–134
Ziemelis K, The future of microelectronics. Nature, 2000, 406: 1021–1023
Corredor C C, Huang Z L, Belfield K D, Morales A R, Bondar M V. Photochromic polymer composites for two-photon 3D optical data storage. Chem Mater, 2007, 19: 5165–5173
Piner R, Zhu J, Xu F, Hong S, Mirkin C. “Dip-Pen” nanolithography. Science, 1999, 283: 661–663
Denk W, Strickler J H, Webb W W. Two-photon laser scanning fluorescence microscopy. Science, 1990, 248: 73–76
Larson D R, Zipfle W R, Williams R M, Clark S W, Bruchez M P, Wise F W, Webb W W. Water-soluble quantum dots for multiphoton fluorescence imaging in vivo. Science, 2003, 300: 1434–1436
Fisher A M R, Murphree A L, Gomer C J. Clinical and preclinical photodynamic therapy. Laser Surg Med, 1995, 17: 2–31
Stiel H, Tenchner K, Paul A. Two-photon excitation of alkyl- substituted magnesium phthalocyanine: Radical formation via higher excited states. J Photochem Photobiol A: Chem, 1994, 80: 289–298
Frederiksen P K, Jorgensen M, Ogilby P R. Two-photon photosensitized production of singlet oxygen. J Am Chem Soc, 2001, 123: 1215–1221
Bhawalkar J D, Kumar N D, Zhao C F, Prasad P N. Two-photon photodynamic therapy. J Clin Laser Med Surg, 1997, 15: 201–204
Zheng Q D, He G S, Prasad P N. п-Conjugated dendritic nanosized chromo phore with enhanced two-photon absorption. Chem Mater, 2005, 17: 6004–6011
Zhao C F, He G S, Bhawalker J D, Park C K, Prasad P N. Newly synthesized dyes and their polymer/glass composites for one- and two-photon pumped solid-state cavity lasing. Chem Mater, 1995, 7: 1979–1983
Cumpston B H, Ananthavel S P, Barlow S, Dyer D L, Ehrilich J E, Erskine L L, Heikal A A, Kuebler S M, Sandy Lee I Y, McCord-Maughon D, Qin J, Röckel H, Rumi M, Wu X L, Marder S R, Perry J W. Two-polymerization initiators for three-dimensional optical data storage and microfabrication. Nature, 1999, 398: 51–54
Kawata S, Sun H B, Tanaka T, Takada K. Finer features for functional microdevices. Nature, 2001, 412: 697–698
Chung S J, Kim K S, Lin T C, He G S, Swiatkiewicz J, Prasad P N. Cooperative enhancement of two-photon absorption in multibranched structures. J Phys Chem B, 1999, 103: 10741–10745
Bhaskar A, Ramakrishna G, Lu Z K, Twieg R, Hales J M, Hagan D J, Stryland E V, Goodson T. Investigation of two-photon absorption properties in branched alkene and alkyne chromophores. J Am Chem Soc, 2006, 128: 11840–11849
Yamasaki K, Joudkazis S, Watanabe M, Sun H B, Matsuo S, Misawa H. Two-photon reading of three-dimensional optical memory in polymethyl-methacrylate films. Appl Phys Lett, 2000, 76: 1000–1002
Day D, Gu M. Formation of voids in a doped polymethylmethacrylate polymer. Appl Phys Lett, 2002, 80: 2404–2406
Jiu H F, Tang H H, Zhou J L, Xu J, Zhang Q J, Xing H, Huang W H, Xia A D. Sm(DBM)3Phen-doped poly(methyl methacrylate) for three-dimensional multilayered optical memory. Opt Lett, 2005, 30: 774–776
Zhou Y J, Chen D Q, Huang W H, Xia A D. Development of the scanning system for confocal laser scanning fluorescence microscope. Opt Precision Eng, 2002, 10: 582–587
Tian Y P, Li L, Zhang J Z, Yang J X, Zhou H P, Wu J Y, Sun P P, Tao L M, Guo Y H, Wang C K, Xin H, Huang W H, Tao X T, Jiang M H. Investigations and facile synthesis of a series of novel multi- functional two-photon absorption materials. J Mater Chem, 2007, 17: 3646–3654
Cui C M, Zhou H P, Zhu C H, Wu J Y. Tris(4-acetyphenyl)amine. Acta Crystallograph Sect E: Strut Rep Online, 2006, 62: O1762–O1763
Sheldrick G M. SHELXTL V5.1 Software Reference Manual. Madison, Wisconsin: Bruker AXS, Inc. 1997
Drobizhev M, Rebane A, Sigel C, Elandaloussi E H, Spangler C W. Picosecond dynamics of excitations studied in three generations of new 4,4′-bis (diphenylamino) stilbene-based dendrimers. Chem Phys Lett, 2000, 325: 375–382
Xu C, Webb W W. Multiphoton fluorescence excitation: New spectral windows for biological nonlinear microscopy. J Opt Soc Am B, 1996, 13: 481–491
Albota M A, Xu C, Webb W W. Two-photon fluorescence excitation cross sections of biomolecular probes from 690 to 960 nm. Appl Opt, 1998, 37: 7352–7356
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Supported by the National Natural Science Foundation of China (Grant Nos. 50532030, 20771001 & 50703001), the Team for Scientific Innovation Foundation of Anhui Province (Grant No. 2006KJ007TD), the Education Committee of Anhui Province (Grant No. KJ2007B089), and Outstanding Doctoral Dissertation Cultivation Fund of Anhui University (Grant No. 20072004)
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Cheng, L., Li, L., Sun, P. et al. Synthesis, structure and nonlinear optical properties of two novel two-photon absorption chromophores. Sci. China Ser. B-Chem. 52, 529–534 (2009). https://doi.org/10.1007/s11426-009-0026-y
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DOI: https://doi.org/10.1007/s11426-009-0026-y