Synthesis of optically active green fluorescent π-conjugated fluorene polymers having chiral Schiff bases in the side chain

被引:21
作者
Asai, Kengo
Konishi, Gen-ichi
Sumi, Kentaro
Kawauchi, Susumu
机构
[1] Meguro-ku, Tokyo 152-8552
关键词
CHIROPTICAL PROPERTIES; POLYFLUORENES; POLYMERIZATION; COPOLYMERS; ELECTROLUMINESCENCE; PHOTOLUMINESCENCE; PHENYLACETYLENE; CONFORMATION; AGGREGATION; OLIGOMERS;
D O I
10.1039/b9py00268e
中图分类号
O63 [高分子化学(高聚物)];
学科分类号
070305 ; 080501 ; 081704 ;
摘要
The synthesis of optically active poly(fluorene-alt-chiral iminofluorene)s using 1-phenylethylamine as a chiral auxiliary is described. Optically active polyfluorenes were synthesized by the palladium-catalyzed Suzuki-Miyaura coupling polymerization of 9,9'-dioctylfluorene-2,7-bis(trimethyleneborate) with a chiral Schiff base monomer (imino group modified-fluorene). The obtained polymers showed intense green emission with high quantum efficiency. Analysis of the circular dichroism data of the optically active polymers indicates that the polymers exhibit various highly-ordered regular structures in solution.
引用
收藏
页码:321 / 325
页数:5
相关论文
共 51 条
[1]   Blue organic light emitting devices with improved colour purity and efficiency through blending of poly(9,9-dioctyl-2,7-fluorene) with an electron transporting material [J].
Ahn, Jin H. ;
Wang, Changsheng ;
Perepichka, Igor F. ;
Martin, R. Bryce B. ;
Petty, Michael C. .
JOURNAL OF MATERIALS CHEMISTRY, 2007, 17 (29) :2996-3001
[2]   CHIRAL HELICAL CONFORMATION OF THE POLYPHENYLACETYLENE HAVING OPTICALLY-ACTIVE BULKY SUBSTITUENT [J].
AOKI, T ;
KOKAI, M ;
SHINOHARA, K ;
OIKAWA, E .
CHEMISTRY LETTERS, 1993, (12) :2009-2012
[3]   Helix-sense-selective polymerization of phenylacetylene having two hydroxy groups using a chiral catalytic system [J].
Aoki, T ;
Kaneko, T ;
Maruyama, N ;
Sumi, A ;
Takahashi, M ;
Sato, T ;
Teraguchi, M .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (21) :6346-6347
[4]   The built-in potential in blue polyfluorene-based light-emitting diodes [J].
Bodrozic, Vladimir ;
Brown, Thomas M. ;
Mian, Shabbir ;
Caruana, Daren ;
Roberts, Matthew ;
Phillips, Nathan ;
Halls, Jonathan J. ;
Grizzi, Ilaria ;
Burroughes, Jeremy H. ;
Cacialli, Franco .
ADVANCED MATERIALS, 2008, 20 (12) :2410-+
[5]   A new poly(2,7-dibenzosilole) derivative in polymer solar cells [J].
Boudreault, Pierre-Luc T. ;
Michaud, Alexandre ;
Leclerc, Mario .
MACROMOLECULAR RAPID COMMUNICATIONS, 2007, 28 (22) :2176-2179
[6]   Synthesis and luminescence properties of three novel polyfluorene copolymers [J].
Charas, A ;
Morgado, J ;
Martinho, JMG ;
Alcácer, L ;
Lim, SF ;
Friend, RH ;
Cacialli, F .
POLYMER, 2003, 44 (06) :1843-1850
[7]   Highly emissive iptycene-fluorene conjugated copolymers: Synthesis and photophysical properties [J].
Chen, Zhihua ;
Bouffard, Jean ;
Kooi, Steven E. ;
Swager, Timothy M. .
MACROMOLECULES, 2008, 41 (18) :6672-6676
[8]  
CHI CY, 2007, MACROMOL RAPID COMM, V28, P2176
[9]   Chiral architectures from macromolecular building blocks [J].
Cornelissen, JJLM ;
Rowan, AE ;
Nolte, RJM ;
Sommerdijk, NAJM .
CHEMICAL REVIEWS, 2001, 101 (12) :4039-4070
[10]   New alternative copolymer constituted of fluorene and triphenylamine units with a tunable -CHO group in the side chain. Quantitative transformation of the -CHO group to -CH=CHAr groups and optical and electrochemical properties of the polymers [J].
Fang, Q ;
Yamamoto, T .
MACROMOLECULES, 2004, 37 (16) :5894-5899