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One- and Two-Photon Spectroscopy of Donor−Acceptor−Donor Distyrylbenzene Derivatives: Effect of Cyano Substitution and Distortion from Planarity

Pond, Stephanie J. K. and Rumi, Mariacristina and Levin, Michael D. and Parker, Timothy C. and Beljonne, David and Day, Michael W. and Brédas, Jean-Luc and Marder, Seth R. and Perry, Joseph W. (2002) One- and Two-Photon Spectroscopy of Donor−Acceptor−Donor Distyrylbenzene Derivatives: Effect of Cyano Substitution and Distortion from Planarity. Journal of Physical Chemistry A, 106 (47). pp. 11470-11480. ISSN 1089-5639. https://resolver.caltech.edu/CaltechAUTHORS:20170619-073344361

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Abstract

The one- and two-photon spectroscopic properties of four symmetrically substituted donor−acceptor−donor distyrylbenzenes with either di-n-butyl- or diphenylamino donor groups and cyano acceptor groups are reported. It has been found that the position of the substitution of the electron-withdrawing cyano groups on the central phenylene ring as compared to the vinylene bond strongly affects the observed properties. In particular, the molecules with cyano substitution on the α-carbon of the vinylene linkage are characterized by weak fluorescence, short fluorescence lifetimes, and two-photon cross sections (δ) that are comparable to analogous molecules with no acceptor groups. In contrast, the molecules with acceptor substitution on the central phenylene ring are strongly fluorescent and have δ values roughly twice those of the vinyl-substituted molecules. These results are discussed in terms of the larger deviation of the conjugated backbone from planarity and the smaller distance between the donors and acceptors when the cyano groups are substituted on the vinylene carbon rather than the central phenylene ring.


Item Type:Article
Related URLs:
URLURL TypeDescription
http://dx.doi.org/10.1021/jp0267104DOIArticle
http://pubs.acs.org/doi/abs/10.1021/jp0267104PublisherArticle
http://pubs.acs.org/doi/suppl/10.1021/jp0267104PublisherSupporting Information
Additional Information:© 2002 American Chemical Society. Received 7 August 2002. Published online 2 November 2002 Published in print 1 November 2002. This material is based upon work supported by the National Science Foundation under Grant No. CHE-0107105 and CHE-0078819, the Office for Naval Research (Grant No. N00014-95-1-1319 and N00014-01-1-0615), the Air Force Office of Scientific Research (Grant No. F49620-02-1-0358), and the AFOSR Defense University Research Instrumentation Program (Grant No. F49620-99-1-0161), which are gratefully acknowledged. The work in Mons has been partly supported by the Belgian Federal Government “Inter-University Attraction Pole 5/3” and FNRS. We thank Stephen Barlow, David Carrig, Stephen M. Kuebler, and Wim Wenseleers for technical assistance.
Funders:
Funding AgencyGrant Number
NSFCHE-0107105
NSFCHE-0078819
Office for Naval Research (ONR)N00014-95-1-1319
Office for Naval Research (ONR)N00014-01-1-0615
Air Force Office of Scientific ResearchF49620-02-1-0358
AFOSR Defense University Research Instrumentation ProgramF49620-99-1-0161
Belgian Federal Government “Inter-University Attraction Pole 5/3"UNSPECIFIED
Fonds de la Recherche Scientifique (FNRS)UNSPECIFIED
Issue or Number:47
Record Number:CaltechAUTHORS:20170619-073344361
Persistent URL:https://resolver.caltech.edu/CaltechAUTHORS:20170619-073344361
Official Citation:One- and Two-Photon Spectroscopy of Donor−Acceptor−Donor Distyrylbenzene Derivatives:  Effect of Cyano Substitution and Distortion from Planarity Stephanie J. K. Pond, Mariacristina Rumi, Michael D. Levin, Timothy C. Parker, David Beljonne, Michael W. Day, Jean-Luc Brédas, Seth R. Marder, and Joseph W. Perry The Journal of Physical Chemistry A 2002 106 (47), 11470-11480 DOI: 10.1021/jp0267104
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:78315
Collection:CaltechAUTHORS
Deposited By: Ruth Sustaita
Deposited On:19 Jun 2017 16:18
Last Modified:03 Oct 2019 18:07

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