Journal
JOURNAL OF PHYSICAL CHEMISTRY C
Volume 112, Issue 49, Pages 19699-19709Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jp8065635
Keywords
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Funding
- Polish Ministry of Research and Higher Education
- Volkswagen Foundation
- CNR of Italy [PM.P04.10]
- COST D31
- Deutsche Forschungsgemeinschaft
- Fonds der Chemischen Industrie
- Robert A. Welch Foundation [E-680]
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A multichromophoric system, TPA-C-PI, possessing a corrole as the central unit linked to perylene bisimide and N-[4-(phenylethynyl)phenyl]-N,N-diphenylamine was efficiently synthesized, as were the component dyads C-PI and C-TPA. The combination of known methodologies with the newest synthetic advances in Pd-coupling reactions enabled a six-step preparation of the final compounds in a convergent fashion. Several different synthetic strategies were investigated, and one with Sonogashira coupling involved in the final step was successful. Electrochemical and spectroscopic studies confirmed a weak coupling between the component units in the triad which was characterized by an extensive absorption throughout the 300-700 nm region. Photophysical measurements showed efficient energy transfer to occur from the diphenylacetylene substituted aromatic amine (99%) and perylene bisimide unit (100%) to the corrole and subsequent electron transfer from the corrole to perylene bisimide (97% efficient). The final charge separated state in TPA-C-PI was identified as TPA-C+-PI-, with a lifetime of 1.9 ns, similar to that of C+-PI- (2.3 ns). The charge separated state with charges on the extreme components, TPA(+)-C-PI-, is not formed for thermodynamic reasons.
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