Electronic Characterization of Dimethyl 1,2-Dihydropyrrolo1,2-alphaquinoxaline-2,3-dicarboxylate in Solution and in the Solid State

Keisuke Hirano; Seiji Yamaoka; Satoshi MinakataMitsuo Komatsu

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Electronic Characterization of Dimethyl 1,2-Dihydropyrrolo1,2-alphaquinoxaline-2,3-dicarboxylate in Solution and in the Solid State

机译：1,2-二氢吡咯并1,2-alpha喹喔啉-2,3-二羧酸二甲酯在溶液和固态中的电子表征

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Dimethyl 1,2-dihydropyrrolo1,2-aquinoxaline-2,3-cicarboxylate is red colored in the solid state, while it is a small molecule and has no hydrogen-bonding interaction. This unusual color property was investigated by means of electronic characterization in solution and in the solid state. The push-pull system from electron-donating pyrrole nitrogen to the electron-withdrawing 3-methoxycarbonyl moiety causes a spectral shift to an orange color in the visible region. An X-ray structure analysis indicated that these polar molecules (mu=7.6 D) are arranged in a zig-zag fashion so as to minimize the electrostatic energy. As a consequence, the absorption band is presumably shifted toward longer wave-lengths by about 60 nm (about 2508 cm~(-1)) in going from a solution to the solid state. These results lead to a large wave-lengths by about 60 nm (about 2508 cm~(-1)) in going from a solution to the solid state. These results lead to a large batho-chromic shift in the absorption spectrum, resulting in the red color of this compound in the solid state.

机译：1,2-二氢吡咯并[1,2-a]喹喔啉-2,3-环羧酸二甲酯在固态下呈红色，而它是一种小分子，没有氢键相互作用。通过溶液和固态的电子表征来研究这种不寻常的颜色特性。从供电子吡咯氮到吸电子的 3-甲氧羰基部分的推拉系统导致可见光区域的光谱偏移为橙色。X射线结构分析表明，这些极性分子（mu=7.6 D）呈锯齿形排列，以最小化静电能。因此，在从溶液到固态的过程中，吸收带可能向更长的波长移动了约 60 nm（约 2508 cm~（-1））。这些结果导致从溶液到固态的长约为 60 nm（约 2508 cm~（-1））。这些结果导致吸收光谱中较大的深色位移，导致该化合物在固态下呈红色。

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《Bulletin of the Chemical Society of Japan》 |2002年第9期|2075-2078|共4页
作者
Keisuke Hirano; Seiji Yamaoka; Satoshi MinakataMitsuo Komatsu;
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Department of Applied Chemistry, Graduate School of Engineering, Osaka University, Yamadaoka 2-1, Suita Osaka 565-0871Department of Applied Chemistry, Graduate School of Engineering, Osaka University, Yamadaoka 2-1, Suita Osaka 565-0871Department of Appli;

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中图分类化学;化学工业;
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Electronic Characterization of Dimethyl 1,2-Dihydropyrrolo1,2-alphaquinoxaline-2,3-dicarboxylate in Solution and in the Solid State

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