Synthesis and Two-Photon Absorption Properties of Hyperbranched Diketo-Pyrrolo-Pyrrole Polymer with Triphenylamine as the Core

被引:69
作者
Jiang, Yihua [1 ,2 ]
Wang, Yaochuan [3 ]
Hua, Jianli [1 ,2 ]
Qu, Sanyin [1 ,2 ]
Qian, Shiqiong [3 ]
Tian, He [1 ,2 ]
机构
[1] E China Univ Sci & Technol, Inst Fine Chem, Key Lab Adv Mat, Shanghai 200237, Peoples R China
[2] E China Univ Sci & Technol, Dept Chem, Shanghai 200237, Peoples R China
[3] Fudan Univ, Dept Phys, Shanghai 200433, Peoples R China
关键词
conjugated polymers; diketo-pyrrolo-pyrrole; dyes/pigments; synthesis; triphenylamine; two-photon; NONLINEAR-OPTICAL PROPERTIES; CROSS-SECTIONS; PHOTOPHYSICAL PROPERTIES; ULTRAFAST DYNAMICS; ONE-PHOTON; DERIVATIVES; CHROMOPHORES; FLUORESCENCE; EXCITATION; FLUOROPHORES;
D O I
10.1002/pola.23493
中图分类号
O63 [高分子化学(高聚物)];
学科分类号
070305 ; 080501 ; 081704 ;
摘要
A novel hyperbranched polyyne (hb-DPP) with triphenylamine as the core, 2,5-dioctylpyrrolo [3,4-c]pyrrole-1,4 (2H,5H)-dione (DPP) as the connecting unit has been designed and synthesized by Glaser-Hay oxidative coupling reaction, which was characterized by IR, NMR, UV-vis, FL, and GPC. The polymer exhibits high molecular weight (M, up to similar to 6.55 x 10(4) Da) and is readily soluble in common organic solvents such as toluene, chloroform, tetrahydrofuran, N,N-dimethyl formamide and so on. The one- and two-photon absorption (TPA) properties have been investigated. The TPA cross section of the polymer was measured by open-aperture Z-scan experiment using 140 ferntosecond (fs) pulse, and the TPA cross section for hb-DPP was determined to be 579 GM per repeating unit at wavelength of 800 nm. In tetrahydrofuran, hb-DPP exhibits intense frequency up-converted fluorescence with the peak located at 584 nm under the excitation of 800 nm fs pulses. (C) 2009 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem 47: 4400-4408, 2009
引用
收藏
页码:4400 / 4408
页数:9
相关论文
共 56 条
[1]   Novel heterocycle-based two-photon absorbing dyes [J].
Abbotto, A ;
Beverina, L ;
Bozio, R ;
Facchetti, A ;
Ferrante, C ;
Pagani, GA ;
Pedron, D ;
Signorini, R .
ORGANIC LETTERS, 2002, 4 (09) :1495-1498
[2]   Design of organic molecules with large two-photon absorption cross sections [J].
Albota, M ;
Beljonne, D ;
Brédas, JL ;
Ehrlich, JE ;
Fu, JY ;
Heikal, AA ;
Hess, SE ;
Kogej, T ;
Levin, MD ;
Marder, SR ;
McCord-Maughon, D ;
Perry, JW ;
Röckel, H ;
Rumi, M ;
Subramaniam, C ;
Webb, WW ;
Wu, XL ;
Xu, C .
SCIENCE, 1998, 281 (5383) :1653-1656
[3]   Red electroluminescence from a 1,4-diketopyrrolo[3,4-c]pyrrole (DPP)-based conjugated polymer [J].
Beyerlein, T ;
Tieke, B ;
Forero-Lenger, S ;
Brütting, W .
SYNTHETIC METALS, 2002, 130 (02) :115-119
[4]   Building symmetric two-dimensional two-photon materials [J].
Bhaskar, Ajit ;
Guda, Ramakrishna ;
Haley, Michael M. ;
Goodson, Theodore, III .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (43) :13972-13973
[5]  
Bhawalkar J D, 1997, J Clin Laser Med Surg, V15, P201
[6]   Trinaphthylamines as Robust Organic Materials for Two-Photon-Induced Fluorescence [J].
Bordeau, Guillaume ;
Lartia, Remy ;
Metge, Germain ;
Fiorini-Debuisschert, Celine ;
Charra, Fabrice ;
Teulade-Fichou, Marie-Paule .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (50) :16836-+
[7]   Fluorescence resonance energy transfer in a novel two-photon absorbing system [J].
Brousmiche, DW ;
Serin, JM ;
Fréchet, JMJ ;
He, GS ;
Lin, TC ;
Chung, SJ ;
Prasad, PN .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (06) :1448-1449
[8]   Synthesis and characterization of novel red-emitting alternating copolymers based on fluorene and diketopyrrolopyrrole derivatives [J].
Cao, DR ;
Liu, QL ;
Zeng, WJ ;
Han, SH ;
Peng, JB ;
Liu, SP .
JOURNAL OF POLYMER SCIENCE PART A-POLYMER CHEMISTRY, 2006, 44 (08) :2395-2405
[9]   Strong, low-energy two-photon absorption in extended amine-terminated cyano-substituted phenylenevinylene oligomers [J].
Chung, SJ ;
Rumi, M ;
Alain, V ;
Barlow, S ;
Perry, JW ;
Marder, SR .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (31) :10844-10845
[10]   Two-photon properties and excitation dynamics of poly(p-phenylenevinylene) derivatives carrying phenylanthracene and branched alkoxy pendents [J].
Chung, SJ ;
Maciel, GS ;
Pudavar, HE ;
Lin, TC ;
He, GS ;
Swiatkiewicz, J ;
Prasad, PN ;
Lee, DW ;
Jin, JI .
JOURNAL OF PHYSICAL CHEMISTRY A, 2002, 106 (33) :7512-7520