論文

査読有り
2008年7月

Structural properties and degree of intramolecular charge transfer of an N-alkyl indoline-tricyanoquinodimethane system

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN
  • Tsuyoshi Murata
  • ,
  • Kazukuni Nishimura
  • ,
  • Yuichiro Enomoto
  • ,
  • Genki Honda
  • ,
  • Yasuhito Shimizu
  • ,
  • Akihiro Otsuka
  • ,
  • Gunzi Saito

81
7
開始ページ
869
終了ページ
884
記述言語
英語
掲載種別
研究論文(学術雑誌)
DOI
10.1246/bcsj.81.869
出版者・発行元
CHEMICAL SOC JAPAN

A series of intramolecular charge-transfer compounds comprised of 1-alkyl-3,3-dimethyl-2-methyleneindoline (I-n, donor, n = alkyl chain length; 1-8, 10, 14, 16, 18, 20, and 22) and 7,8,8-tricyanoquinodimethane (=2-(4'-cyanomethylene-2'.5'-cyclohexadienylidene)malononitrile (3CNQ), acceptor) moieties linked through a pi-bond, I-n-3CNQ were prepared. and their structures are discussed. The melting points of the I-n-3CNQ solids decreased with increasing alkyl chain length until reaching a minimum point (95 degrees C) at n = 18, and then began to gradually increase, indicating self-aggregation of the alkyl chains. The I-n-3CNQ derivatives with long alkyl chains (n >= 6) produced supercooled liquids displaying conspicuous color changes after melting. Diverse molecular packing patterns were observed in the crystal structures. Most I-n-3CNQ derivatives formed face-to-face and/or side-by-side dimeric motif's to cancel net dipole moments. I-20-3CNQ formed a two-dimensional bilayer structure by pi-stacking and self-assembly of the alkyl chains. Two types of molecular conformation, which significantly affect the electronic structures, were observed to be dependent on the alkyl chain length. A parameter to evaluate the degree of intramolecular charge transfer, namely bond length ratio, was proposed: it exhibited good agreement with solvatochromic shifts and molecular orbital calculations.

リンク情報
DOI
https://doi.org/10.1246/bcsj.81.869
CiNii Articles
http://ci.nii.ac.jp/naid/10021076916
Web of Science
https://gateway.webofknowledge.com/gateway/Gateway.cgi?GWVersion=2&SrcAuth=JSTA_CEL&SrcApp=J_Gate_JST&DestLinkType=FullRecord&KeyUT=WOS:000258738600010&DestApp=WOS_CPL
ID情報
  • DOI : 10.1246/bcsj.81.869
  • ISSN : 0009-2673
  • eISSN : 1348-0634
  • CiNii Articles ID : 10021076916
  • Web of Science ID : WOS:000258738600010

エクスポート
BibTeX RIS