Synthesis, characterization, and physical properties of monodisperse oligo(p-phenyleneethynylene)s

被引:53
作者
Zhou, CZ [1 ]
Liu, TX [1 ]
Xu, JM [1 ]
Chen, ZK [1 ]
机构
[1] Inst Mat Res & Engn, Singapore 117602, Singapore
关键词
D O I
10.1021/ma021656a
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 new stepwise synthesis method for the preparation of precisely defined oligo(p-phenyleneethynylene)s (OPEs) is described. High-purity monomer, trimer, pentamer, heptamer, and nonamer of OPEs with dihexyloxy side groups and trimethylsilyl (TMS) or thioacetyl (SAc) terminals have been synthesized. The structures of the oligomers were characterized by H-1 NMR, C-13 NMR, and elemental analysis. DSC studies show narrow and well-developed melting and crystallization peaks, indicating the high perfection of the crystals formed in these oligomers. Optical microscopy was used for investigating the supramolecular morphology of solid-state films of pentamer with TMS end groups, as an example. Numerous dendrites with a spherulitic size of ca. 50mum were observed. UV-vis absorption and photoluminescence (PL) spectra in both dilute solution and films show a gradual red shift of the lambda(max) from trimer to nonamer. At the nonamer stage, the optical maximum is approaching a limit of convergence.
引用
收藏
页码:1457 / 1464
页数:8
相关论文
共 44 条
[1]  
[Anonymous], 1997, ELECT MAT OLIGOMER A
[2]   Soluble regioregular polythiophene derivatives as semiconducting materials for field-effect transistors [J].
Bao, ZN ;
Lovinger, AJ .
CHEMISTRY OF MATERIALS, 1999, 11 (09) :2607-2612
[3]   The exciton binding energy in luminescent conjugated polymers [J].
Bredas, JL ;
Cornil, J ;
Heeger, AJ .
ADVANCED MATERIALS, 1996, 8 (05) :447-&
[4]   Are single molecular wires conducting? [J].
Bumm, LA ;
Arnold, JJ ;
Cygan, MT ;
Dunbar, TD ;
Burgin, TP ;
Jones, L ;
Allara, DL ;
Tour, JM ;
Weiss, PS .
SCIENCE, 1996, 271 (5256) :1705-1707
[5]   Poly(aryleneethynylene)s: Syntheses, properties, structures, and applications [J].
Bunz, UHF .
CHEMICAL REVIEWS, 2000, 100 (04) :1605-1644
[6]   Electron transfer at electrodes through conjugated "molecular wire" bridges [J].
Creager, S ;
Yu, CJ ;
Bamdad, C ;
O'Connor, S ;
MacLean, T ;
Lam, E ;
Chong, Y ;
Olsen, GT ;
Luo, JY ;
Gozin, M ;
Kayyem, JF .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (05) :1059-1064
[7]   Insertion, conductivity, and structures of conjugated organic oligomers in self-assembled alkanethiol monolayers on Au{111} [J].
Cygan, MT ;
Dunbar, TD ;
Arnold, JJ ;
Bumm, LA ;
Shedlock, NF ;
Burgin, TP ;
Jones, L ;
Allara, DL ;
Tour, JM ;
Weiss, PS .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (12) :2721-2732
[8]   Determination of the molecular electrical properties of self-assembled monolayers of compounds of interest in molecular electronics [J].
Fan, FRF ;
Yang, JP ;
Dirk, SM ;
Price, DW ;
Kosynkin, D ;
Tour, JM ;
Bard, AJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (10) :2454-2455
[9]   Structural order in conjugated oligothiophenes and its implications on opto-electronic devices [J].
Fichou, D .
JOURNAL OF MATERIALS CHEMISTRY, 2000, 10 (03) :571-588
[10]   Synthesis of α,ω-difunctionalized oligo- and poly(p-phenyleneethynylene)s [J].
Francke, V ;
Mangel, T ;
Mullen, K .
MACROMOLECULES, 1998, 31 (08) :2447-2453