Synthesis, Structure, Chromatic Properties, and Induced Circular Dichromism of Polydiacetylenes with an Extended Conjugated System in the Side Chain

被引:8
作者
Dei, Satoshi [1 ]
Matsumoto, Akikazu [1 ]
机构
[1] Osaka City Univ, Grad Sch Engn, Dept Appl Chem, Sumiyoshi Ku, Osaka 5588585, Japan
关键词
CD spectrum; chiral polymer; conjugating polymer; radical polymerization; solid-state polymerization; solvatochromism; UV-vis absorption; SOLID-STATE POLYMERIZATION; ORGANIC INTERCALATION SYSTEM; HYDROGEN-BOND NETWORKS; TOPOCHEMICAL POLYMERIZATION; STEREOREGULAR POLY((4-CARBOXYPHENYL)ACETYLENE); MACROMOLECULAR STEREOCHEMISTRY; CHIRALITY ASSIGNMENT; HELICAL POLYMERS; GUEST MOLECULES; THERMOCHROMISM;
D O I
10.1002/macp.200800488
中图分类号
O63 [高分子化学(高聚物)];
学科分类号
070305 ; 080501 ; 081704 ;
摘要
We synthesized PDAs with a 4-carboxyphenyl substituent directly connected to the conjugating main chain in order to investigate the effects of the side chain structure on the chromatic properties of the polymers. A series of 1,3-alkadiynyl-4-benzoic acids (m,Ph-DA-CO2H) and their 1-naphthylmethylammonium salts (m,Ph-DA-Naph) were under UV and gamma-ray irradiation. The resulting poly(m,Ph-DA-CO2H)s had absorption bands in their UV-vis spectra in a wavelength region longer than those for the poly(m,Ph-DA-Naph)s and the other PDAs. We report the first example of the induced circular dichromism of poly(m,Ph-DA-CO2H) in the combination with a chiral (1-cyclohexyl)ethylamine in the dispersion and in the solid state by an acid/base interaction. prepared and polymerized
引用
收藏
页码:11 / 21
页数:11
相关论文
共 81 条
[21]   OBSERVATION OF CLUSTER FORMATION IN AN IONOMER [J].
GALAMBOS, AF ;
STOCKTON, WB ;
KOBERSTEIN, JT ;
SEN, A ;
WEISS, RA ;
RUSSELL, TP .
MACROMOLECULES, 1987, 20 (12) :3091-3094
[22]   Low molecular-mass gelators with diyne functional groups and their unpolymerized and polymerized gel assemblies [J].
George, M ;
Weiss, RG .
CHEMISTRY OF MATERIALS, 2003, 15 (15) :2879-2888
[23]  
Green MM, 1999, ANGEW CHEM INT EDIT, V38, P3139
[24]   MAJORITY RULES IN THE COPOLYMERIZATION OF MIRROR-IMAGE ISOMERS [J].
GREEN, MM ;
GARETZ, BA ;
MUNOZ, B ;
CHANG, HP ;
HOKE, S ;
COOKS, RG .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (14) :4181-4182
[25]   MACROMOLECULAR STEREOCHEMISTRY - A COOPERATIVE DEUTERIUM-ISOTOPE EFFECT LEADING TO A LARGE OPTICAL-ROTATION [J].
GREEN, MM ;
ANDREOLA, C ;
MUNOZ, B ;
REIDY, MP ;
ZERO, K .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (12) :4063-4065
[26]   MACROMOLECULAR STEREOCHEMISTRY - THE OUT-OF-PROPORTION INFLUENCE OF OPTICALLY-ACTIVE CO-MONOMERS ON THE CONFORMATIONAL CHARACTERISTICS OF POLYISOCYANATES - THE SERGEANTS AND SOLDIERS EXPERIMENT [J].
GREEN, MM ;
REIDY, MP ;
JOHNSON, RJ ;
DARLING, G ;
OLEARY, DJ ;
WILLSON, G .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (16) :6452-6454
[27]   A field guide to foldamers [J].
Hill, DJ ;
Mio, MJ ;
Prince, RB ;
Hughes, TS ;
Moore, JS .
CHEMICAL REVIEWS, 2001, 101 (12) :3893-4011
[28]   Peptide amphiphile nanofibers with conjugated polydiacetylene backbones in their core [J].
Hsu, Lorraine ;
Cvetanovich, Gregory L. ;
Stupp, Samuel I. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (12) :3892-3899
[29]   Metal ion modulated organization and function of the Langmuir-Blodgett films of amphiphilic diacetylene: Photopolymerization, thermochromism, and supramolecular chirality [J].
Huang, X ;
Jiang, SG ;
Liu, MH .
JOURNAL OF PHYSICAL CHEMISTRY B, 2005, 109 (01) :114-119
[30]   Chirality of photopolymerized organized supramolecular polydiacetylene films [J].
Huang, X ;
Liu, MH .
CHEMICAL COMMUNICATIONS, 2003, (01) :66-67