Novel 5‐(Benzo[b]thiophen‐3‐yl)pyridine‐3‐carbaldehyde (BTPA) Functionalization Framework For Modulating Fullerene Electronics
نویسندگان
چکیده
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 λmax of BTFP (λmax,BTFP=290 nm and λmax,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 λmax of BTFP (relative to PCMB) is likely to contribute to improved light absorption of a suitable donor for photovoltaic applications.
منابع مشابه
Synthesis of novel 1,3,4-oxadiazole derivatives as potential antimicrobial agents.
Some new 3-acetyl-5-(3-chloro-1-benzo[b]thiophen-2-yl)-2-substituted phenyl-2,3-dihydro-1,3,4-oxadiazoles and 2-(3-chloro-1-benzo[b]thiophen-2-yl)-5-substituted phenyl-1,3,4-oxadiazoles have been synthesized and evaluated for antimicrobial activity. Initially, 3-chloro-1-benzo[b]thiophene-2-carbonyl chloride (1) was prepared from cinnamic acid in the presence of chlorobenzene and thionyl chlori...
متن کاملDesign and synthesis of novel antimicrobial acyclic and heterocyclic dyes and their precursors for dyeing and/or textile finishing based on 2-N-acylamino-4,5,6,7-tetrahydro-benzo[b]thiophene systems.
A series of novel polyfunctionalized acyclic and heterocyclic dye precursors and their respective azo (hydrazone) counterpart dyes and dye precursors based on conjugate enaminones and/or enaminonitrile moieties were synthesized. The dyes and their precursors are based on 2-cyano-N-(3-cyano-4,5,6,7-tetrahydrobenzo[b]thiophen-2-yl)-acetamide, 2-ethoxycarbonyl-N-(3-cyano-4,5,6,7-tetrahydrobenzo[b]...
متن کاملSynthesis, docking studies and biological evaluation of benzo[b]thiophen-2-yl-3-(4-arylpiperazin-1-yl)-propan-1-one derivatives on 5-HT1A serotonin receptors.
A series of novel benzo[b]thiophen-2-yl-3-(4-arylpiperazin-1-yl)-propan-1-one derivatives 6a-f, 7a-f and their corresponding alcohols 8a-f were synthesized and evaluated for their affinity towards 5-HT(1A) receptors. The influence of arylpiperazine moiety and benzo[b]thiophene ring substitutions on binding affinity was studied. The most promising analogue, 1-(benzo[b]thiophen-2-yl)-3-(4-(pyridi...
متن کاملSynthesis of some New Imidazolones and 1,2,4-Triazoles Bearing Benzo[b]thiophene Nucleus as Antimicrobial Agents
2-Phenyl-1-(3?,5?-dichloro-2?-benzo(b)thiophenoylamino)-4-arylidine-5-imidazolones (2a-j) were prepared from the 2-hydrazinocarbonyl-3,5-dichlorobenzo[b]thiophene 1 by the reaction with different oxazolinone which were prepared by the condensation of substituted benzaldehyde with benzoyl glycine in presence of sodium acetate and acetic anhydride. Reaction of 1 with different aromatic isothiocya...
متن کاملMICROWAVE ASSISTED SYNTHESIS AND SPECTRAL STUDIES OF 2- THIOPHEN-2-YLMETHYLENE-2,3,4,9-TETRAHYDRO-CARBAZOL-1-ONE, 3-THIOPHEN-2-YL-4,5-DIHYDRO-10H-2-OXA-1,10-DIAZA- CYCLOPENTA[a]CARBAZOLE AND 3-THIOPHEN-2-YL-2,4,5,10-TETRAHYDRO- 1,2,10-TRIAZA-CYCLOPENTA[a]CARBAZOLE DERIVATIVES
Microwave assisted new aldol condensation reaction of 1-oxo-1,2,3,4tetrahydrocarbazoles 1 with thiophene-2-carbaldehyde 2 in the presence of alcoholic KOH affords a single product 2-Thiophen-2-ylmethylene-2,3,4,9-tetrahydro-carbazol-1-one 3. 3 on irradiation with hydroxylamine hydrochloride yielded 3-Thiophen-2-yl-4,5-dihydro-10H-2-oxa-1,10-diazacyclopenta[a]carbazole 4 and 3 on irradiation wit...
متن کامل