Controlled Regioregularity in Oligo(2-methoxy-5-(2鈥?ethylhexyloxy)-1,4-phenylenevinylenes

详细信息    查看全文

• 作者：Xinju Zhu ; Kyle N. Plunkett
• 刊名：Journal of Organic Chemistry
• 出版年：2014
• 出版时间：August 1, 2014
• 年：2014
• 卷：79
• 期：15
• 页码：7093-7102
• 全文大小：446K
• ISSN：1520-6904

文摘

A series of three pentameric derivatives of 2-methoxy-5-(2鈥?ethylhexyloxy)-p-phenylenevinylenes (2鈥?b>4), with varying degrees of side chain regioregularity, was prepared. The oligomerization chemistry was carried out using repetitive Horner鈥揥adsworth鈥揈mmons (HWE) reactions of precisely substituted aryl rings with four different substituents. The resulting oligomers were characterized by nuclear magnetic resonance spectroscopy (NMR), cyclic voltammetry (CV) and absorption spectroscopy in solution and in thin films. Each of the oligomers gave discrete ¹H and ¹³C NMR spectra. The regioregular pentamer (2) displayed the most resolution between signals and suggests those nuclei reside in more unique chemical environments than the regiorandom pentamers (3 and 4). The solution phase electronic (CV) and absorption properties of each of the new oligomers were found to be essentially identical. In contrast, the thin film absorption spectra were not equivalent. The more regioregular pentamers (2 and 3) possessed a new, red-shifted shoulder structure that suggests the packing order is heavily influenced by side chain regioregularity even at the pentamer level.