π-Conjugated Polymers Consisting of Isothianaphthene and Dialkoxy-p-phenylene Units: Synthesis, Self-Assembly, and Chemical and Physical Properties

被引:17
作者
Yamamoto, Takakazu [1 ]
Usui, Motoaki [1 ]
Ootsuka, Haruki [1 ]
Iijima, Takayuki [1 ]
Fukumoto, Hiroki [1 ]
Sakai, Yoshimasa [2 ]
Aramaki, Shinji [2 ]
Yamamoto, Hiroshi M. [3 ]
Yagi, Takehiko [4 ]
Tajima, Hiroyuki [4 ]
Okada, Taku [4 ]
Fukuda, Takashi [5 ]
Emoto, Akira [5 ]
Ushijima, Hirobumi [5 ]
Hasegawa, Miki [6 ]
Ohtsu, Hideki [6 ]
机构
[1] Tokyo Inst Technol, Chem Resources Lab, Midori Ku, Yokohama, Kanagawa 2268503, Japan
[2] Mitsubishi Chem Grp Sci & Technol Res Ctr Inc, Aoba Ku, Yokohama, Kanagawa 2278502, Japan
[3] RIKEN, Wako, Saitama 3510198, Japan
[4] Univ Tokyo, Inst Solid State Phys, Kashiwa, Chiba 2778581, Japan
[5] Natl Inst Adv Ind Sci & Technol, Tsukuba, Ibaraki 3058565, Japan
[6] Aoyama Gakuin Univ, Coll Sci & Engn, Dept Chem & Biol Sci, Kanagawa 2298558, Japan
关键词
conducting polymers; conjugated polymers; isothianaphthene; polyaromatics; self-assembly; TAIL-TYPE POLY(3-HEXYLTHIOPHENE-2,5-DIYL); OPTICAL-PROPERTIES; MOLECULAR ALIGNMENT; ELECTROCHEMICAL PROPERTIES; LIQUID-CRYSTALLINE; SOLID STRUCTURE; FILMS; THIOPHENE; CONDUCTIVITY; OLIGOMERS;
D O I
10.1002/macp.201000246
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 series of pi-conjugated alternating copolymers consisting of Th-ITN-Th and p-C6H2(OR)(2) units were synthesized. XRD indicated that the copolymers assume an interdigitation packing mode, and UV-Vis spectra revealed a strong tendency for self-assembly. Upon molecular assembly of the copolymer, the UV-Vis absorption shifted by about 100 nm to a longer wavelength from that of the single molecule. The copolymers underwent electrochemical oxidation (or p-doping) and reduction (or n-doping) at 0.2 and -2.0 V versus Ag+/Ag, respectively. A p-doped copolymer film showed an electrical conductivity of 182 S.cm(-1), and the temperature dependence of electrical conductivity was measured. The copolymer showed piezochromism and served as a p-channel material for a field-effect transistor.
引用
收藏
页码:2138 / 2147
页数:10
相关论文
共 84 条
[11]  
DAHLENKAMP T, 1994, MACROMOL CHEM PHYS, V195, P1933
[12]  
Fichou D., 1999, HDB OLIGO AND POLYTH
[13]   REGIODEFINED SUBSTITUTED POLY(2,5-THIENYLENE)S [J].
GALLAZZI, MC ;
CASTELLANI, L ;
MARIN, RA ;
ZERBI, G .
JOURNAL OF POLYMER SCIENCE PART A-POLYMER CHEMISTRY, 1993, 31 (13) :3339-3349
[14]  
GEBEYEHU D, 2002, SYNTHETIC MET, P279
[15]   CRYSTALLOGRAPHIC STUDY OF POLYMERS EXHIBITING SIDE-CHAIN CRYSTALLIZATION [J].
HSIEH, HWS ;
POST, B ;
MORAWETZ, H .
JOURNAL OF POLYMER SCIENCE PART B-POLYMER PHYSICS, 1976, 14 (07) :1241-1255
[16]   Synthesis of aza-analogues of poly(isothianaphthene) [J].
Huskic, M ;
Vanderzande, D ;
Gelan, J .
SYNTHETIC METALS, 1999, 99 (02) :143-147
[17]   Hopping transport in conductive heterocyclic oligomers: Reorganization energies and substituent effects [J].
Hutchison, GR ;
Ratner, MA ;
Marks, TJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (07) :2339-2350
[18]   Main-chain-type 8-quinolinol polymers: Synthesis, optical properties, and complex formation with metals [J].
Iijima, Takayuki ;
Kuroda, Shin-ichi ;
Yamamoto, Takakazu .
MACROMOLECULES, 2008, 41 (05) :1654-1662
[19]   SYNTHESIS AND CHARACTERISTIC PROPERTIES OF POLY(NAPHTHO[2,3-C]THIOPHENE) AS A SERIES OF FUSED-RING CONDUCTING POLYMERS ANALOGOUS TO POLY(ISOTHIANAPHTHENE) [J].
IKENOUE, Y .
SYNTHETIC METALS, 1990, 35 (03) :263-270
[20]   CONFORMATIONAL-CHANGES OF POLY(3-ALKYLTHIOPHENE)S WITH TEMPERATURE AND PRESSURE [J].
IWASAKI, K ;
FUJIMOTO, H ;
MATSUZAKI, S .
SYNTHETIC METALS, 1994, 63 (02) :101-108