Novel 5-(Benzo[b]thiophen-3-yl)pyridine-3-carbaldehyde (BTPA) Functionalization Framework For Modulating Fullerene Electronics.

Autor: John SV; SensorLab, Department of Chemistry University of Western Cape Robert Sobukwe Road, Bellville Cape Town 7535 South Africa., De Filippo CC; Chemical Sciences Department University of Padova Via Marzolo 1 35131 Padova Italy., Silvestrini S; Chemical Sciences Department University of Padova Via Marzolo 1 35131 Padova Italy., Maggini M; Chemical Sciences Department University of Padova Via Marzolo 1 35131 Padova Italy., Iwuoha E; SensorLab, Department of Chemistry University of Western Cape Robert Sobukwe Road, Bellville Cape Town 7535 South Africa.
Jazyk: angličtina
Zdroj: ChemistryOpen [ChemistryOpen] 2017 Apr 04; Vol. 6 (3), pp. 354-359. Date of Electronic Publication: 2017 Apr 04 (Print Publication: 2017).
DOI: 10.1002/open.201600174
Abstrakt: Through a cycloaddition reaction, fullerene (C 60 ) was derivatized with a novel organic compound 5-(benzo[b]thiophen-3-yl)pyridine-3-carbaldehyde to form the processable and stable 3-(benzo[b]thiophene-3yl)-5-fullero-1-methylpyrrolidinepyridine (BTFP) compound. BTFP exhibits close similarities to phenyl-C61-butyric-acid-methyl-ester (PCBM) in terms of first reduction potential values (-0.62 and -0.61 V vs. Ag/AgCl, for BTFP and PCBM, respectively) and lowest occupied molecular orbital (LUMO) energy level values (3.93 eV in both cases). In chloroform, BTFP exhibits a bathochromic shift in the λ max of BTFP ( λ max, BTFP=290 nm and λ max, PCBM=260 nm), owing to the grafted benzo[b]thiophene-3-yl)pyridine moiety. Despite the similarity in LUMO (3.93 eV) energy values, BTFP and PCBM differ in their luminescence-quenching ability. The bathochromic shift in the λ max of BTFP (relative to PCMB) is likely to contribute to improved light absorption of a suitable donor for photovoltaic applications.
Databáze: MEDLINE
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