Synthesis and characterization of polyene chromophores with hydroxyl functionalization

被引：1
作者：
Tututtila, Tero [1 ]
Lipsonen, Jarkko [1 ]
Huuskonen, Juhani [1 ]
Rissanen, Kari [1 ]
机构：
[1] Univ Jyvaskyla, Dept Chem, Nanosci Ctr, FIN-40014 Jyvaskyla, Finland
来源：
DYES AND PIGMENTS | 2008年 / 77卷 / 02期
关键词：
polyenes; chromophores; conjugated aldehydes; cyanoacetamide; Knoevenagel condensation;
D O I：
10.1016/j.dyepig.2007.06.003
中图分类号：
O69 [应用化学];
学科分类号：
081704 ;
摘要：
Eight hydroxyl functionalized donor-acceptor polyene chromophores 3-10 were synthesized and characterized. Knoevenagel condensation reaction of aromatic polyenals with 2-cyanoacetamide derivatives was utilized to synthesize chromophores with all-E configuration. Chromophores of this kind can be attached covalently to polymers or functionalized with dendrons in order to tune the properties. The structures of the molecules were verified by H-1 NMR, C-13 NMR, ESI-TOF mass spectrometry and UV-vis measurements. Reduced bond-length alternation of the molecules in DMSO-d(6) solution were observed by calculating the average difference of the vicinal coupling constants between adjacent CH CH and CH-CH bonds of the conjugated bridge. Thermal stability of the molecules was determined by thermogravimetric analysis (TG). The decomposition temperatures varied between 190 and 256 degrees C. All measured compounds displayed absorption maximum in visible region, and found to exhibit positive solvatochromic behavior. (c) 2007 Elsevier Ltd. All rights reserved.
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收藏
页码：357 / 362
页数：6
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