Electron donor-acceptor compounds: Exploiting the triptycene geometry for the synthesis of porphyrin quinone diads, triads, and a tetrad
Speck M, Wiehe A, Senge MO, Schäfer A, Tannert S, Kurreck H, Röder B (2001)
Publication Type: Journal article, Original article
Publication year: 2001
Journal
Original Authors: Wiehe A., Senge M., Schäfer A., Speck M., Tannert S., Kurreck H., Röder B.
Publisher: Elsevier
Book Volume: 57
Pages Range: 10089-10110
Journal Issue: 51
DOI: 10.1016/S0040-4020(01)01052-3
Abstract
Rigidly and covalently linked porphyrin quinones are well established as model compounds for studying photo-induced electron transfer (PET) reactions like those occurring during the primary processes of photosynthesis. In this context, the synthesis of a number of porphyrin quinones is reported in which one or two porphyrin electron donors are connected to either one or two quinone electron acceptors, resulting in diad, triad, and tetrad model systems, respectively. The porphyrin(s) and the quinone(s) are linked by triptycene, 1,4-phenylene, and cis- or trans-1,4-cyclohexylene bridges. The use of the 1,4-phenylene, and cis- or trans-1,4-cyclohexylene bridges results in donor-acceptor compounds with the same number of bonds between donor and acceptor(s), but differing in distance and orientation. Analysis of the H NMR spectra confirmed the chair conformation for the cis- and trans-cyclohexylene-linked diads and triads. NOE experiments gave information about the spatial arrangement of the target compounds. The key compounds in the syntheses of all these new PET model systems are the triptycene quinones, which are formed via a [π+π]-cyclo-addition between an anthracene derivative and a suitable quinone. The triptycene system enforces a rigid orientation on the quinone acceptor(s) in the final model system. Evidence is given that the triptycene system has further potential for constructing tailor-made donor-acceptor compounds. © 2001 Elsevier Science Ltd. All rights reserved.
Authors with CRIS profile
Involved external institutions
Freie Universität Berlin
Germany (DE)
Humboldt-Universität zu Berlin
Germany (DE)
Trinity College Dublin
Ireland (IE)
Germany (DE)
Humboldt-Universität zu Berlin
Germany (DE)
Trinity College Dublin
Ireland (IE)
How to cite
APA:
Speck, M., Wiehe, A., Senge, M.O., Schäfer, A., Tannert, S., Kurreck, H., & Röder, B. (2001). Electron donor-acceptor compounds: Exploiting the triptycene geometry for the synthesis of porphyrin quinone diads, triads, and a tetrad. Tetrahedron, 57(51), 10089-10110. https://dx.doi.org/10.1016/S0040-4020(01)01052-3
MLA:
Speck, Marcus, et al. "Electron donor-acceptor compounds: Exploiting the triptycene geometry for the synthesis of porphyrin quinone diads, triads, and a tetrad." Tetrahedron 57.51 (2001): 10089-10110.
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