Synthesis and electronic properties of pi-extended flavins

Mataranga-Popa, L. N. and Torje, I. and Ghosh, T. and Leitl, M. J. and Spaeth, A. and Novianti, M. L. and Webster, R. D. and Koenig, B. (2015) Synthesis and electronic properties of pi-extended flavins. ORGANIC & BIOMOLECULAR CHEMISTRY, 13 (40). pp. 10198-10204. ISSN 1477-0520, 1477-0539

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Abstract

Flavin derivatives with an extended pi-conjugation were synthesized in moderate to good yields from aryl bromides via a Buchwald-Hartwig palladium catalyzed amination protocol, followed by condensation of the corresponding aromatic amines with violuric acid. The electronic properties of the new compounds were investigated by absorption and emission spectroscopy, cyclic voltammetry, density functional theory (DFT) and time dependent density functional theory (TDDFT). The compounds absorb up to 550 nm and show strong luminescence. The photoluminescence quantum yields.PL measured in dichloromethane reach 80% and in PMMA (poly(methyl methacrylate)) 77%, respectively, at ambient temperature. The electrochemical redox behaviour of p-extended flavins follows the mechanism previously described for the parent flavin.

Item Type: Article
Uncontrolled Keywords: MOLECULAR-ORBITAL METHODS; VISIBLE-LIGHT; MODEL SYSTEMS; BASIS-SETS; FLAVOENZYME ACTIVITY; RIBOFLAVIN; REDUCTION; ENERGY; OXYGEN; FLAVOPROTEINS;
Subjects: 500 Science > 540 Chemistry & allied sciences
Divisions: Chemistry and Pharmacy > Institut für Organische Chemie > Lehrstuhl Prof. Dr. Burkhard König
Depositing User: Dr. Gernot Deinzer
Date Deposited: 29 Jul 2019 08:21
Last Modified: 29 Jul 2019 08:21
URI: https://pred.uni-regensburg.de/id/eprint/6186

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