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

ABSTRACT: Through a cycloaddition reaction, fullerene (C₆₀) 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 ?_max of BTFP (?_max,BTFP=290?nm and ?_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 ?_max of BTFP (relative to PCMB) is likely to contribute to improved light absorption of a suitable donor for photovoltaic applications.

SUBMITTER: John SV 

PROVIDER: S-EPMC5474664 | biostudies-literature | 2017 Jun

REPOSITORIES: biostudies-literature