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Fingerprints of Through-Bond and Through-Space Exciton and Charge Conjugations in Linearly Extended [2,2]Paracyclophanes

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Zafra, José L. and Molina Ontoria, Agustín and Mayorga Burrezo, Paula and Peña Avarez, Miriam and Samoc, Marek and Szeremeta, Janusz and Ramínez, Francisco J. and Lovander, Matthew D. and Droske, Christopher J. and Pappenfus, Ted M. and Echegoyen, Luis and López Navarrete, Juan T. and Martín, Nazario and Casado, Juan (2017) Fingerprints of Through-Bond and Through-Space Exciton and Charge Conjugations in Linearly Extended [2,2]Paracyclophanes. Journal of the American Chemical Society, 139 . pp. 3095-3105. ISSN 0002-7863 (Print) 1520-5126 (Online)

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Official URL: https://pubs.acs.org/doi/pdf/10.1021/jacs.6b12520



Abstract

New stilbenoid and thiophenic compounds terminally functionalized with donor-donor, acceptor-acceptor and donoracceptor moieties and substituting a central [2,2]paracyclophane unit have been prepared and their properties interpreted in terms of through-bond and through space conjugations. A description of the excited state properties based on photophysical data and with focus on the participation of the central [2,2]paracyclophane, or “phane” state, in competition with through-bond conjugation in the arms has been conducted. To this end, one-photon absorption and emission spectroscopy, as a function of temperature, of solvent polarity in solution and of pressure in solid state have been carried out. Furthermore, the analysis of charge delocalization in the face-toface [2,2]paracyclophane part in the neutral state and in the oxidized species (dications and trications) has been assessed allowing to elucidate the vibrational Raman fingerprint of charge delocalization in these systems. Thus, a complementary approach to “intermolecular” excitation and charge delocalization has been presented in [2,2]paracyclophane model systems by means of the pertinent spectroscopic techniques.


Item Type:Article
Subjects:Sciences > Chemistry > Chemistry, Organic
ID Code:46376
Deposited On:08 Feb 2018 11:32
Last Modified:28 Feb 2018 00:01

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