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自从四十年代末环丙烷的三角杂化模型提出以后,人们就试图用实验来证实环丙烷的不饱和性。但这一问题的研究随后就导致了一场争论。仅就紫外光谱而言,不少工作表明环丙烷环具有一定的不饱和性,在某种程度上可以与相连的不饱和体系发生共轭,但也有些工作却得出了不同的结论。本文合成了一个新的反-1,2-双芳杂环取代的环丙烷类化合物Et-BDCP,研究了其紫外吸收光谱及其荧光激发与发射光谱,并通过与Et-BPDS、Et-BPDE和Et-PDPDP光谱性质的比较,以及用MNDO方法对模型化合物(1—8)所进行的模拟量子化学计算,证明了环丙烷环可以在某种程度上与不饱和体系共轭。
Since the proposition of the cyclopropane triangular hybrid model in the late 1940’s, one has attempted to experimentally confirm the unsaturation of cyclopropane. However, the research on this issue subsequently led to a debate. In terms of the UV spectrum alone, a lot of work shows that the cyclopropane ring has some degree of unsaturation and can be conjugated to some degree with unsaturated systems. However, some work leads to different conclusions. In this paper, a new trans-1,2-bis-heterocyclic ring-substituted cyclopropane Et-BDCP was synthesized and its UV absorption spectra, fluorescence excitation and emission spectra were studied. Comparison of the spectral properties with Et-PDPDP and the simulated quantum chemical calculations of the model compounds (1-8) using the MNDO method demonstrate that the cyclopropane rings can be somewhat conjugated to the unsaturated systems.