反应详情

A method for producing the compound according to the present invention is not particularly limited and can be any method. The compound represented by the chemical formula (1) or (2) can be synthesized (produced) easily by refluxing appropriate perylene tetracarboxylic acid bis(ω-alkenylimide) or perylene tetracarboxylic acid bis(ω,ω-alkadienyl imide) and appropriate oligosiloxane in toluene in the presence of a Karstedt catalyst, for example. The Karstedt catalyst is, for example, a catalyst obtained by coordinating platinum with vinylsiloxane. The Karstedt catalyst can be prepared from H2PtCl6 and vinylsiloxane, for example. More specifically, the compound represented by the chemical formula (1) can be synthesized according to the following scheme 1, for example, and the compound represented by the chemical formula (2) can be synthesized by the following scheme 2, for example. In the following scheme 1, for example, perylene tetracarboxylic acid bis(allylimide) (compound (6), m=1, n=1) and 1,1,1,3,3,5,5-heptamethyl trisiloxane are heated in toluene preferably in the presence of a Karstedt catalyst. Thereafter the solvent is distilled off, and then, the crude product thus obtained is purified by a silica gel column chromatography (eluent: dichloromethane) and re-precipitation with methanol. Thus, the intended perylene tetracarboxylic acid bis(1,1,1,3,3,5,5-heptamethyltrisiloxanyl propylimide) (compound (1), m=1, n=1) can be obtained. In the following scheme 2, for example, perylene tetracarboxylic acid bis(1,8-nonadiene-5-ylimide) (compound (10), m=1, n=1) and 1,1,1,3,3,5,5-heptamethyl trisiloxane are heated in toluene in the presence of a Karstedt catalyst, and thereafter, a purification is performed in the same manner as in the scheme 1. Thus, perylene tetracarboxylic acid bis{di-(1,1,1,3,3,5,5-heptamethyl trisiloxanyl butyl)-methylimide}(compound (2), m=1, n=1) can be obtained. Perylene tetracarboxylic acid bis(allylimide) (compound (6), m=1, n=1) as a starting material can be obtained by heating perylene tetracarboxylic acid anhydride (PTCDA) and allylamine in quinolone in the presence of zinc acetate (the following scheme 1). Perylene tetracarboxylic acid bis(1,8-nonadiene-5-ylimide) (compound (10), m=1, n=1) as a starting material can be obtained in the same manner as for the compound (6) except that 1,8-nonadiene-5-ylamine (compound (9), m=1, n=1) is used as substitute for allylamine (the following scheme 2). In the scheme 2, “DEAD” represents diethyl azodicarboxylate. The same applies hereinafter. The case where m=1 and n=1 is described above, and also in the case where m and n are numeral values other than 1, a synthesis can be performed according to the above-described method. The reaction conditions such as a reaction temperature and a reaction time are not particularly limited. The above-described reaction conditions can be set or changed as appropriate with reference to the examples described below, a known similar reaction, and the like, for example. The reaction solvent also is not limited by the description and can be changed as appropriate.

1. customa purification