@article{oai:soar-ir.repo.nii.ac.jp:00019890, author = {Shoji, Taku and Ito, Shunji}, issue = {66}, journal = {CHEMISTRY-A EUROPEAN JOURNAL}, month = {Nov}, note = {First published: 07 Aug 2017, We describe the synthesis and properties of azulene-substituted 1,1,4,4-tetracyanobutadienes (AzTCBDs) and heteroazulenyl TCBDs. TCBD derivatives were prepared in good to excellent yields through reaction of the corresponding 1-ethynylazulenes with tetracyanoethylene (TCNE). In contrast, the reaction between propargyl alcohols and the 1-azulenyl group in TCNE generated 2-aminofuran derivatives, which were transformed into 6-aminofulvenes with a 1-azulenyl substituent upon treatment with several amines. The optical and electrochemical properties of the AzTCBDs were clarified by UV/Vis and voltammetry. The AzTCBD derivatives exhibited electrochromism, showing a multi-step color change under electrochemical redox conditions. The multistage redox properties of AzTCBDs could be useful for the development of novel organic electronic materials., Article, CHEMISTRY-A EUROPEAN JOURNAL. 95(1):16696-16709 (2017)}, pages = {16696--16709}, title = {Azulene-Based Donor-Acceptor Systems: Synthesis, Optical, and Electrochemical Properties}, volume = {23}, year = {2017} }