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

新型有机p电子分子的开发及其在彩色材料中的应用

• 批准号: 18550174
• 负责人: OGURA Katsuyuki
• 金额: $ 2.6万
• 依托单位: Chiba University
• 依托单位国家: 日本
• 项目类别: Grant-in-Aid for Scientific Research (C)
• 财政年份: 2006
• 资助国家: 日本
• 起止时间: 2006 至 2007
• 项目状态: 已结题
• 来源: https://kaken.nii.ac.jp/grant/KAKENHI-PROJECT-18550174/
• 关键词: Metallic Luster; Tricyanoethenyl Derivatives; Organic π-System; Thin Film; Electron-Conducting; 電気伝導性

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.

本研究旨在开发具有三氰基乙烯基团的各种功能材料(如有色材料)，使中性有机π-电子体系之间发生分子间的相互作用。2007年，我们研究了1-芳基-2-(2-噻吩基)-5-(5-三氰基-2-噻吩基)吡咯(1)晶体诱导金属光泽的起源，以及具有TCE基团的新型分子的发展，形成了具有金属光泽的薄膜，取得了以下成果。1)金属光泽来源的理论研究。用平面偏振光研究了π电子分子(1)的排列与金属光泽的关系，阐明了π-分子的连续排列是三氰基乙烯基团与吡咯π-体系分子间相互作用的结果。这一结论也得到了从头算分子轨道方法(B3LYP/6-31G(D))的理论计算支持。2)利用TCE基团开发稳定的金属光泽薄膜去年我们发现，含有两个或两个以上N-[4-(三氰基乙烯基)苯基]苯胺基(TCPA)的化合物形成了具有金属光泽的薄膜。此外，我们一直在研究什么样的含TCPA基团的化合物可以得到稳定的具有金光泽的薄膜。结果表明，3，5-二甲基苯甲酸甲酯的甲基基团为TCPA，苯甲酸甲酯的3-位和5-位基团为TCPA，形成了具有金属光泽的稳定薄膜。此外，还发现苯甲酸酯在3-和5-位上有两个TCPA基团，形成了具有金属光泽的稳定薄膜。

项目成果

Convenient Synthesis of 3,3,3‐Trifluoropropanoic Acid by Hydrolytic Oxidation of 3,3,3‐Trifluoropropanal Dimethyl Acetal.

• DOI: 10.1002/chin.200822051
• 发表时间: 2008-05
• 期刊: ChemInform
• 作者: T. Komata;Shinya Akiba;K. Hosoi;K. Ogura

The cross-aldol reaction of hexafluoroacetone(HEA) with ketones catalyzed by an acid

酸催化六氟丙酮(HEA)与酮的交叉羟醛反应

• 发表时间: 2007
• 期刊: Joumal of Fluorine Chemistry 128
• 作者: A. Ashida;A. Fujita;Y. Shim;K. Wakita;A. Nakahira;Takeo Komata
• 通讯作者: Takeo Komata

Formation of metal-lustrous organic crystals from 2-aryl-1-(4-methoxyphenyl)-5-(5-tricyanoethenyl-2-thienyl)pyrroles

• DOI: 10.1016/j.tet.2005.12.055
• 发表时间: 2006-03-13
• 期刊: TETRAHEDRON
• 影响因子: 2.1
• 作者: Ogura, K;Ooshima, K;Matsumoto, S
• 通讯作者: Matsumoto, S

Novel p-electronic compounds having N- [p- tricyanoethenyl) phenyl] anilino groups: the effect of alkoxyl group on their ability to form a thin layer with metallic luster

具有N-[对-三氰基乙烯基）苯基]苯胺基的新型p电子化合物：烷氧基对其形成金属光泽薄层能力的影响

• 发表时间: 2008
• 作者: Katsuyuki Ogura;Motoki Tanaka;Motohiro Akazome;and Shoji Matsumoto
• 通讯作者: and Shoji Matsumoto

Metallic luster of 1-aryl-2- (2-thienyli-5-[ 5- (tricyanoethenyl) -2-thienyl] pyrrol crystals: Relationship between the arrangement of pai-molecules and reflection spectra

1-芳基-2-(2-噻吩基-5-[ 5-(三氰基乙烯基)-2-噻吩基]吡咯晶体的金属光泽：pai分子排列与反射光谱之间的关系

• 发表时间: 2007
• 作者: Katsuyuki Ogura;Motoki Tanaka;Motohiro Akazome;and Shoji Matsumoto;小倉 克之;小具健一;Ken-ich Ogu and Katsuyuki Ogura
• 通讯作者: Ken-ich Ogu and Katsuyuki Ogura