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Models for photochemical electron transfer at fixed distances. Porphyrin-bicyclo[2.2.2]octane-quinone and porphyrin-bisbicyclo[2.2.2]octane-quinone

Joran, Alvin D. and Leland, Burt A. and Geller, George G. and Hopfield, John J. and Dervan, Peter B. (1984) Models for photochemical electron transfer at fixed distances. Porphyrin-bicyclo[2.2.2]octane-quinone and porphyrin-bisbicyclo[2.2.2]octane-quinone. Journal of the American Chemical Society, 106 (20). pp. 6090-6092. ISSN 0002-7863. https://resolver.caltech.edu/CaltechAUTHORS:20160511-151848505

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Abstract

We report the syntheses of three rigidly linked side-by-side porphyrinquinone molecules 2-4 whose edge-to-edge distances are fixed at 6, 10, and 14 Å (Figure 1). The spacer units bicyclo[2.2.2]octane and bibicyclo[2.2.2]octane prevent translational displacement and only allow rotational freedom. Our preliminary studies of the fluorescence yields of both the free base PLQ 2a-4a and Zn PLQ 2b-4b systems, relative to 1, a similar porphyrin not equipped with a quinone, reveal a distance dependence. This suggests that 2-4 will be useful systems for studying the incremental effect of distance on photochemical electron transfer from excited-state porphyrins to quinones.


Item Type:Article
Related URLs:
URLURL TypeDescription
http://dx.doi.org/10.1021/ja00332a062DOIArticle
http://pubs.acs.org/doi/abs/10.1021/ja00332a062PublisherArticle
ORCID:
AuthorORCID
Dervan, Peter B.0000-0001-8852-7306
Additional Information:© 1984 American Chemical Society. Received June 11, 1984. We are grateful to the National Science Foundation (CHE-8305790 and DMR-8107494) and to the Southern California Regional NMR Facility (NSF Grant 7916324) for generous support of this research. Contribution No. 7046, Division of Chemistry and Chemical Engineering, California Institute of Technology, Pasadena, California 91125.
Funders:
Funding AgencyGrant Number
NSFCHE-8305790
NSFDMR-8107494
NSF7916324
Other Numbering System:
Other Numbering System NameOther Numbering System ID
Division of Chemistry and Chemical Engineering7046
Issue or Number:20
Record Number:CaltechAUTHORS:20160511-151848505
Persistent URL:https://resolver.caltech.edu/CaltechAUTHORS:20160511-151848505
Official Citation:Models for photochemical electron transfer at fixed distances. Porphyrin-bicyclo[2.2.2]octane-quinone and porphyrin-bisbicyclo[2.2.2]octane-quinone Alvin D. Joran, Burt A. Leland, George G. Geller, John J. Hopfield, and Peter B. Dervan Journal of the American Chemical Society 1984 106 (20), 6090-6092 DOI: 10.1021/ja00332a062
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:67020
Collection:CaltechAUTHORS
Deposited By: Victoria Brennan
Deposited On:19 May 2016 20:51
Last Modified:26 Nov 2019 11:15

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