Electrochromism based on the charge transfer process in a ferrocene–BODIPY molecule

• Published in: Tetrahedron Vol. 65; no. 40; pp. 8373 - 8377
• Main Authors: Yin, Xiaodong, Li, Yongjun, Li, Yuliang, Zhu, Yulan, Tang, Xueling, Zheng, Haiyan, Zhu, Daoben
• Format: Journal Article
• Language: English
• Published: OXFORD Elsevier Ltd 03.10.2009; Elsevier
• Subjects: Charge transfer; Chemistry; Chemistry, Organic; Density functional theoretical calculation; Electrochemistry; Electrochromism; Exact sciences and technology; General and physical chemistry; Heterocyclic compounds; Kinetics and mechanisms; Miscellaneous; Miscellaneous (electroosmosis, electrophoresis, electrochromism, electrocrystallization, ...); Organic chemistry; Organic metallic compound; Physical Sciences; Preparations and properties; Reactivity and mechanisms; Science & Technology; Electrochromism; Organic metallic compound; Charge transfer; Density functional theoretical calculation; POLYMERS; ENERGY; BORON; APPROXIMATION; COMPLEXES; HETEROACENES; ABSORPTION; Transition element complexes; Metal ion; NMR spectrometry; Metallocene; Chemical reduction; Energy gap; Amine borane; Optical properties; Reaction mechanism; Oxidation; Chemical synthesis; Organic compounds; Frontier orbital; Reuse; Organometallic compound; Theoretical study; Experimental study; Ferrocene; Iron Organic compounds; Electrochemical properties; Electrochemistry; Density functional method; Cations; Nitrogen boron heterocycle; Fluorescent compound; Ultraviolet visible spectrometry
• ISSN: 0040-4020; 1464-5416
• DOI: 10.1016/j.tet.2009.08.008

A new type of donor–acceptor molecule DiFc-B combined ferrocene and BODIPY unit has been synthesized, and the NMR spectra, photophysical property, and electrochemical property were studied. The in situ spectro-electrochemical experiment was carried out, a notable absorption change had been observed under oxidative potential, and a recovery could happen under reductive potential and this process could repeat for several times. Such a phenomenon also happened when oxidative metal ion was added into the solution of DiFc-B. In order to study the mechanism of the electrochromism, the theoretical calculation was performed, and the result shows a D (ferrocene)–π–A (BODIPY) system. The energy gap between the HOMO and LUMO had a good consistence with the electrochemical experiment and UV–vis data. The calculation of the frontier orbital belonging to the cation state of DiFc-B shows the directional change of the D–π–A system, which supplied a theoretical basis of the electrochromism. [Display omitted]