Solid-State Photopolymerization of a Shape-Persistent Macrocycle with Two 1,8-Diazaanthracene Units in a Single Crystal

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• 作者：Ming Li ; A. Dieter Schl眉ter ; Junji Sakamoto
• 刊名：The Journal of the American Chemical Society
• 出版年：2012
• 出版时间：July 18, 2012
• 年：2012
• 卷：134
• 期：28
• 页码：11721-11725
• 全文大小：301K
• 年卷期：v.134,no.28(July 18, 2012)
• ISSN：1520-5126

文摘

A macrocyclic monomer with two opposing 1,8-diazaanthracene units is polymerized in a single crystal by a photochemically induced [4 + 4] cycloaddition reaction between neighboring monomers in which the anthracene units are stacked face-to-face at the critical Schmidt distance. The severe structural changes associated with this are minimized by the monomer design, wherein the linkers between the two opposing photoreactive 1,8-diazaanthracene units are connected to the 4 and 5 positions of the latter, whose spatial positioning is changed the least during dimerization. This helps to keep the monomer鈥檚 overall shape basically unchanged during the polymerization. The resulting new rigid-rod polymer is soluble in its protonated form, and after counterion exchange with a surfactant, it can be depolymerized back into monomer upon relatively mild thermal treatment (120 掳C) in an organic solvent.