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Article Dans Une Revue Tetrahedron Letters Année : 2014

Fluorescent 2-(2′-hydroxybenzofuran)benzoxazole (HBBO) borate complexes: synthesis, optical properties, and theoretical calculations

Julien Massue
Karima Benelhadj
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Siwar Chibani
  • Fonction : Auteur
Gilles Ulrich
Raymond Ziessel
  • Fonction : Auteur

Résumé

The multi-​step synthesis, structural and optical properties of original luminescent borate complexes derived from 2-​(2'-​hydroxybenzofuran)​benzoxazole (HBBO) are reported. Functionalization at position 3 of the benzofuran ring was readily achieved through an electrophilic cyclization key step followed by a Sonogashira cross-​coupling reaction. The optical properties of the resulting boron difluoride dyes highlight different photophys. behaviors depending on the nature of the substitution at position 3 of the benzofuran core (tBu-​phenylacetylene or NnBu2-​phenylacetylene)​. The NnBu2-​phenylacetylene moiety favors a sizeable intramol. charge transfer as evidenced by a strong solvatochromism; a feature further confirmed by ab initio calcns.
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Dates et versions

hal-01088544 , version 1 (28-11-2014)

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Citer

Julien Massue, Karima Benelhadj, Siwar Chibani, Boris Le Guennic, Denis Jacquemin, et al.. Fluorescent 2-(2′-hydroxybenzofuran)benzoxazole (HBBO) borate complexes: synthesis, optical properties, and theoretical calculations. Tetrahedron Letters, 2014, 55 (30), pp.4136-4140. ⟨10.1016/j.tetlet.2014.06.002⟩. ⟨hal-01088544⟩
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