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Coronenetetraimide-Centered Cruciform Pentamers Containing Multiporphyrin Units: Synthesis and Sequential Photoinduced Energy- and Electron-Transfer Dynamics

Title
Coronenetetraimide-Centered Cruciform Pentamers Containing Multiporphyrin Units: Synthesis and Sequential Photoinduced Energy- and Electron-Transfer Dynamics
Authors
HasobeT.IdaK.SakaiH.OhkuboFukuzumiS.
Ewha Authors
Shunichi FukuzumiKei Okubo
SCOPUS Author ID
Shunichi Fukuzumiscopus; Kei Okuboscopus
Issue Date
2015
Journal Title
Chemistry - A European Journal
ISSN
0947-6539JCR Link
Citation
vol. 21, no. 31, pp. 11196 - 11205
Keywords
dyes/pigmentselectron transferenergy transferporphyrinszinc
Publisher
Wiley-VCH Verlag
Indexed
SCI; SCIE; SCOPUS WOS scopus
Abstract
A series of coronenetetraimide (CorTIm)-centered cruciform pentamers containing multiporphyrin units, in which four porphyrin units are covalently linked to a CorTIm core through benzyl linkages, were designed and synthesized to investigate their structural, spectroscopic, and electrochemical properties as well as photoinduced electron- and energy-transfer dynamics. These systems afforded the first synthetic case of coroneneimide derivatives covalently linked with dye molecules. The steady-state absorption and electrochemical results indicate that a CorTIm and four porphyrin units were successfully characterized by the corresponding reference monomers. In contrast, the steady-state fluorescence measurements demonstrated that strong fluorescence quenching relative to the corresponding monomer units was observed in these pentamers. Nanosecond laser flash photolysis measurements revealed the occurrence of intermolecular electron transfer from triplet excited state of zinc porphyrins to CorTIm. Femtosecond laser-induced transient absorption measurements for excitation of the CorTIm unit clearly demonstrate the sequential photoinduced energy and electron transfer between CorTIm and porphyrins, that is, occurrence of the initial energy transfer from CorTIm (energy donor) to porphyrins (energy acceptor) and subsequent electron transfer from porphyrins (electron donor) to CorTIm (electron acceptor) in these pentamers, whereas only the electron-transfer process from porphyrins to CorTIm was observed when we mainly excite porphyrin units. Finally, construction of high-order supramolecular patterning of these pentamers was performed by utilizing self-assembly and physical dewetting during the evaporation of solvent. Efficient energy conversion systems: Coronenetetraimide (CorTIm)-centered cruciform pentamers containing four porphyrin units covalently linked to a CorTIm core were synthesized (see figure). These systems afforded the first synthetic case of coroneneimide derivatives covalently linked with dye molecules. The sequential photoinduced energy and electron transfer between CorTIm and porphyrins in these pentamers was clearly demonstrated by using femtosecond laser flash photolysis. © 2015 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.
DOI
10.1002/chem.201500766
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자연과학대학 > 화학·나노과학전공 > Journal papers
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