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- W2171697675 abstract "A series of thirteen luminescent tetrahedral borate complexes based on the 2-(2'-hydroxyphenyl)benzoxazole (HBO) core is presented. Their synthesis includes the incorporation of an ethynyl fragment by Sonogashira cross-coupling reaction, with the goal of extending the conjugation and consequently redshifting their emission wavelength. Different regioisomers, substituted in the 3-, 4-, or 5-position of the phenolate side of the HBO core, were studied in order to compare their photophysical properties. The complexes were characterized by X-ray diffraction and NMR, UV/Vis, and emission spectroscopy in solution and in the solid state. In all cases, complexation to boron leads to a donor-acceptor character that impacts their photophysical properties. Complexes with a 3- or 5-substituted fragment display mild to pronounced internal charge transfer (ICT), a feature strengthened by the presence of p-dibutylaminophenylacetylene in the molecular structure, protonation of the nitrogen atom of which leads to a significant blueshift and an increase in quantum yield. On the contrary, when the ethynyl module is grafted on the 4-position, narrow, structured, symmetrical absorption/emission bands are observed. Moreover, the fact that protonation has little effect on the emission maximum wavelength reveals singlet excited-state decay. Solid-state emission properties reveal a redshift compared to solution, explained by tight packing of the π-conjugated systems and the high planarity of the dyes. Subsequent connection of these complexes to other photoactive subunits (BODIPY, Boranil) provides dyads in which efficient cascade energy transfer is observed." @default.
- W2171697675 created "2016-06-24" @default.
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- W2171697675 date "2013-02-27" @default.
- W2171697675 modified "2023-10-18" @default.
- W2171697675 title "Synthesis of Luminescent Ethynyl-Extended Regioisomers of Borate Complexes Based on 2-(2′-Hydroxyphenyl)benzoxazole" @default.
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- W2171697675 doi "https://doi.org/10.1002/chem.201203625" @default.
- W2171697675 hasPubMedId "https://pubmed.ncbi.nlm.nih.gov/23447429" @default.
- W2171697675 hasPublicationYear "2013" @default.
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