Diarylurea-Linked Zinc Porphyrin Dimer as a Dual-Mode Artificial Receptor: Supramolecular Control of Complexation-Facilitated Photoinduced Electron Transfer
Authors:
- 18 March 2003
- journal article
- research article
- Published by American Chemical Society (ACS) in Journal of the American Chemical Society
- Vol. 125 (14) , 4068-4069
Abstract
A novel porphyrinic receptor 1 in which two zinc porphyrins are bridged by two diarylurea linkers was developed for recognition of a viologen derivative (hexyl viologen, HV). The electronic absorption spectra as well as the 1H NMR experiments revealed that the HV molecule was bound to the cleft in 1 mainly through carbonyl dipole-charge interactions to afford a 1:1 complex. From the steady-state fluorescence spectroscopic study, the photoinduced electron transfer (PET) from 1 to HV was extremely facilitated by the receptor−substrate complexation. The receptor 1 also formed a 1:1 complex with 1,4-diazabicyclo[2.2.2]octane (DABCO) through two Zn−N coordination interactions, and, using DABCO as an inhibitor, we suppressed the PET reaction via the substrate exchange.Keywords
This publication has 27 references indexed in Scilit:
- Facile synthesis of cofacial porphyrin dimer and trimer using a diarylurea linkageChemical Communications, 2001
- A Cyclic Dimer of Metalloporphyrin Forms a Highly Stable Inclusion Complex with C60Journal of the American Chemical Society, 1999
- Structural control of co-receptor binding in porphyrin–bipyridinium supramolecular assembliesJournal of the Chemical Society, Perkin Transactions 1, 1998
- Very Efficient Visible-Light-Induced Uphill Electron Transfer at a Self-Assembled Monolayer with a Porphyrin−Ferrocene−Thiol Linked MoleculeJournal of the American Chemical Society, 1997
- Molecular modelling of electron transfer systems by noncovalently linked porphyrin–acceptor pairingChemical Society Reviews, 1997
- Long-range photoinduced electron transfer in an associated but non-covalently linked photosynthetic model systemJournal of the American Chemical Society, 1993
- Near-infrared-excited Fourier transform Raman spectroscopic study of covalently linked porphyrin-viologen compoundsThe Journal of Physical Chemistry, 1993
- Controlled electron transfer between cyclodextrin-sandwiched porphyrin and quinonesJournal of the American Chemical Society, 1993
- 1,2-Phenylene-bridged diporphyrin linked with porphyrin monomer and pyromellitimide as a model for a photosynthetic reaction center: synthesis and photoinduced charge separationJournal of the American Chemical Society, 1993
- Photoinduced electron transfer in supramolecular systems for artificial photosynthesisChemical Reviews, 1992