Synthesis, photophysical, and two-photon absorption properties of elongated phosphane oxide and sulfide derivatives
| Autor: | Jérémy Bell, Isabelle Leray, Mireille Blanchard-Desce, Véronique Michelet, Patrick Y. Toullec, Issa Samb, Valérie Alain‐Rizzo, Delphine Drouin-Kucma, Cédric Rouxel |
|---|---|
| Přispěvatelé: | Laboratoire de Photophysique et Photochimie Supramoléculaires et Macromoléculaires (PPSM), École normale supérieure - Cachan (ENS Cachan)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Chimie et Photonique Moléculaires (CPM), Université de Rennes (UR)-Centre National de la Recherche Scientifique (CNRS), Laboratoire Charles Friedel, Ecole Nationale Supérieure de Chimie de Paris - Chimie ParisTech-PSL (ENSCP), Université Paris sciences et lettres (PSL)-Université Paris sciences et lettres (PSL)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Université Pierre et Marie Curie - Paris 6 (UPMC)-Ecole Nationale Supérieure de Chimie de Paris - Chimie ParisTech-PSL (ENSCP), Université de Rennes 1 (UR1), Université de Rennes (UNIV-RENNES)-Université de Rennes (UNIV-RENNES)-Centre National de la Recherche Scientifique (CNRS) |
| Jazyk: | angličtina |
| Rok vydání: | 2011 |
| Předmět: |
Phosphines
solvatochromism phosphanes Sonogashira coupling Conjugated system Sulfides 010402 general chemistry Photochemistry 01 natural sciences Biochemistry Two-photon absorption Absorption [CHIM]Chemical Sciences two-photon absorption Photons 010405 organic chemistry Chemistry Organic Chemistry Solvatochromism charge transfer Oxides General Chemistry Fluorescence Acceptor 0104 chemical sciences Intramolecular force fluorescence Absorption (chemistry) |
| Zdroj: | Chemistry-An Asian Journal Chemistry-An Asian Journal, 2011, 6 (4), pp.1080-1091. ⟨10.1002/asia.201000681⟩ |
| ISSN: | 1861-4728 |
| DOI: | 10.1002/asia.201000681⟩ |
| Popis: | International audience; A series of rod-shaped and related three-branched push-pull derivatives containing phosphane oxide or phosphane sulfide (PO or PS)a-as an electron-withdrawing group conjugated to electron-donating groups, such as amino or ether groups, with a conjugated rod consisting of arylene-vinylene or arylene-ethynylene building blocksa-were prepared. These compounds were efficiently synthesized by a Grignard reaction followed by Sonogashira coupling. Their photophysical properties including absorption, emission, time-resolved fluorescence, and two-photon absorption (TPA) were investigated with special attention to structure-property relationships. These fluorophores show high fluorescence quantum yields and solvent-dependent experiments reveal that efficient intramolecular charge transfer occurs upon excitation, thereby leading to highly polar excited states, the polarity of which can be significantly enhanced by playing on the end groups and conjugated linker. Rod-shaped and related three-branched systems show similar fluorescence properties in agreement with excitation localization on one of the push-pull branches. By using stronger electron donors or replacing the arylene-ethynylene linkers with an arylene-vinylene one induces significant redshifts of both the low-energy one-photon absorption and TPA bands. Interestingly, a major enhancement in TPA responses is observed, whereas OPA intensities are only weakly affected. Similarly, phosphane oxide derivatives show similar OPA responses than the corresponding sulfides but their TPA responses are significantly larger. Finally, the electronic coupling between dipolar branches promoted by common PO or PS acceptor moieties induces either slight enhancement of the TPA responses or broadening of the TPA band in the near infrared (NIR) region. Such behavior markedly contrasts with triphenylamine-core-mediated coupling, which gives evidence for the different types of interactions between branches. © 2011 WILEY-VCH Verlag GmbH and Co. KGaA, Weinheim. |
| Databáze: | OpenAIRE |
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