Development of Novel Organic p-Electronic Molecules and Their Application to Color Materials

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This research aimed the development of various functional materials (for example color material) having tricyanoethenyl (TCE) group, which makes neutral organic π-electronic systems interact with each others intermolecularly. In 2007, we investigated the origin of the metallic luster induced by 1-aryl-2- (2-thienyl) -5- (5-tricyano-2-thienyl) pyrrole (1) crystals as well as the development of novel molecules having TCE groups that form thin film with metallic luster and, as a result, the following fruitful results were gained. 1) Theoretical Investigation of the origin of the metallic luster. The relationship between the arrangement of the π-electronic molecules (1) and the metallic luster were investigated by the use of plane-polarized light that was irradiated on each plane of the single crystal of 1, elucidating that successive arrangement of the π-molecules in such a manner that tricyanoethenyl group interacts with pyrrole π-system intermolecularly. This conclusion was also supported by the theoretical calculation with the ab initio molecular orbital method (B3LYP/6-31G(d)). 2) Development of Stable Metal-lustrous thin films by the Use of TCE Groups Last year, we found that the compounds having two or more N-[4- (tricyanoethenyl) pheny]anilino (TCPA) groups forms a thin film with metallic luster. Furthermore, we have been investigating what kind of compound having TCPA groups can give a stable thin film with gold-like luster. As a result, it was elucidated that methyl 3, 5-dimethylbenzoate having TCPA at the methyl groups and methyl benzoate having TCPA groups at the 3- and 5-positions form a stable thin film with metallic luster. Furthermore, the benzoate ester that has two TCPA groups at 3- and 5-positions was found to form a stable thin film with metallic luster.