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Orbital Control of the Color and Excited State Properties of Formylated and Fluorinated Derivatives of Azulene^†

Sergey V. Shevyakov,^‡ Hongru Li,^‡ Rajeev Muthyala,^‡ Alfred E. Asato,^‡ John C. Croney,^§ David M. Jameson,^§ and Robert S. H. Liu*^‡

Department of Chemistry, University of Hawaii, 2545 The Mall, Honolulu, Hawaii 96822 and Department of Cell and Molecular Biology, University of Hawaii, 1960 East-West Road, Honolulu, Hawaii 96822

J. Phys. Chem. A, 2003, 107 (18), pp 3295–3299

DOI: 10.1021/jp021605f

Publication Date (Web): April 4, 2003

†

Part of the special issue “George S. Hammond & Michael Kasha Festschrift”.

‡

Department of Chemistry, University of Hawaii.

Department of Cell and Molecular Biology, University of Hawaii.

To whom correspondence should be addressed.

Abstract

New azulene derivatives containing resonantly electron withdrawing formyl and resonantly electron donating fluorine substituents on the seven- as well as the five-member ring have been prepared. Systematic color changes as a result of perturbation of HOMO, LUMO, and LUMO + 1 energies were discussed. Corresponding excited-state properties related to S₂-fluorescence were determined.

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