Mingjung Kuo, Shi-Min Shau, Je-Min Su
Jun 19, 2012
Citations
0
Influential Citations
14
Citations
Journal
Macromolecules
Abstract
In this study, we synthesized a dual-functional building intermediate, 4-(3,3-diethyl-2,4-dioxoazetidin-1-yl)benzoyl chloride (DEDA-BC), from readily available starting materials, including 4-isocyanatobenzoyl chloride and p-tolyl isocyanate. In its iterative syntheses of hard segments, we first treated the highly reactive acid chloride of DEDA-BC with the monoamine (aniline) or the diamine (4,4′-methylenedianiline, 4,4′-MDA) to form first-generation azetidien-2,4-dione intermediates. We then reacted these derivatives with 4-aminobenzylamine at the more-selective azetidine-2,4-dione group of DEDA-BC to form the first-generation of benzyl amine extenders. Using this alternating method, we obtained high yields of supramolecular extenders of various chain lengths (n = 1–3) in a systematic manner, without the need for tedious purification steps, under catalyst-free conditions. The mono- and diamine extenders with numbers of repeating units ranging from one to three were synthesized precisely through this new ...