Azulenocyanine: a new family of phthalocyanines with intense near-IR absorption.
Azulenocyanine, having four azulene units fused to a tetraazaporphyrin skeleton, is a structural isomer of naphthalocyanine. We synthesized the first example of an azulenocyanine from 1,3-di-tert-butyl-5,6-dicyanoazulene. The macrocycle exhibits broad absorption over the visible and near-IR regions far beyond 1000 nm. Theoretical calculations and electrochemical experiments show the LUMO energy level is drastically lowered. Azulenocyanine represents a new type of oxidation-stable near-IR dye.
Muranaka
Atsuya
A
Advanced Elements Chemistry Laboratory, Advanced Science Institute, RIKEN, Wako-shi, Saitama 351-0198, Japan. atsuya-muranaka@riken.jp
Yonehara
Mitsuhiro
M
Uchiyama
Masanobu
M
D000042:Absorption; D052176:Azulenes / Q000737:chemistry*; D007211:Indoles / Q000737:chemistry*; D007259:Infrared Rays; D054833:Isoindoles; D008958:Models, Molecular; D008968:Molecular Conformation; D011166:Porphyrins / Q000737:chemistry*
D052176:Azulenes; D007211:Indoles; D054833:Isoindoles; D011166:Porphyrins; C005525:azulene; C013647:phthalocyanine