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Configuration‐Dependent Photoinduced Electron Transfer in Diastereomeric Naphthalene‐Amino‐Naphthalene Triads |
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| Authors: | Dr Edurne Nuin Dr German Sastre Dr Uwe Pischel Dr Inmaculada Andreu Prof Miguel A Miranda |
| Institution: | 1. Instituto de Tecnología Química UPV‐CSIC, Universitat Politècnica de València, Avenida de los Naranjos s/n, 46022 Valencia (Spain), Fax: (+34)?96‐387‐9444;2. CIQSO‐Centro de Investigación en Química Sostenible y Departamento de Ingeniería Química, Química Física y Química Orgánica, Universidad de Huelva, Campus de El Carmen s/n, 21071 Huelva (Spain);3. Unidad Mixta de Investigación IIS La Fe‐UPV, Hospital Universitari i Politècnic La Fe, Avenida de Fernando Abril Martorell 106, 46026 Valencia (Spain), Fax: (+34)?96‐349‐4420 |
| Abstract: | Novel diastereomeric triads containing two naphthalene chromophores have been designed in which an electron‐donating amine moiety is covalently integrated into the connecting bridge. Photophysical studies (steady‐state and time‐resolved fluorescence) in solvents of different polarity have been performed. A remarkable stereodifferentiation in the intramolecular fluorescence quenching was found in acetonitrile. Laser flash photolysis gave rise to naphthalene‐derived radical cations, which were also quenched by the amine with an even higher degree of stereodifferentiation. The results are in agreement with thermodynamic estimations and indicate that photoinduced electron transfer (PET) is the main quenching pathway. Furthermore, theoretical calculations have allowed us to explain the experimentally observed stereodifferentiation in PET quenching. |
| Keywords: | chromophores electron transfer intramolecular fluorescence quenching singlet– singlet energy transfer stereodifferentiation |