BOPAHY: a doubly chelated highly fluorescent pyrrole–acyl hydrazone –BF2 chromophore

Shandev Pookkandam Parambil; Flip de Jong; Koen Veys; Jianjun Huang; Santhini Pulikkal Veettil; Davy Verhaeghe; Luc Van Meervelt; Daniel Escudero; Mark Van der Auweraer; Wim Dehaen

doi:10.1039/D0CC01131B

BOPAHY: a doubly chelated highly fluorescent pyrrole–acyl hydrazone –BF₂ chromophore†

Shandev Pookkandam Parambil,

^a Flip de Jong,

^b Koen Veys,

^c Jianjun Huang,^a Santhini Pulikkal Veettil,

^a Davy Verhaeghe,

^b Luc Van Meervelt,

^d Daniel Escudero,

^c Mark Van der Auweraer^b and Wim Dehaen

*^a

Author affiliations

* Corresponding authors

^a Molecular Design and Synthesis, Department of Chemistry, KU Leuven, Celestijnenlaan 200F, 3001 Leuven, Belgium
E-mail: wim.dehaen@kuleuven.be

^b Molecular Imaging and Photonics, Department of Chemistry, KU Leuven, Celestijnenlaan 200F, 3001 Leuven, Belgium

^c Quantum Chemistry and Physical Chemistry Section, Department of Chemistry, KU Leuven, Celestijnenlaan 200F, 3001 Leuven, Belgium

^d Biochemistry, Molecular and Structural Biology, Department of Chemistry, KU Leuven, Celestijnenlaan 200F, B-3001 Leuven, Belgium

Abstract

New easily functionalisable and highly fluorescent BOPAHY chromophores are synthesised via a one-pot two-step reaction starting from commercially available pyrrole-2-carbaldehydes and respective acyl hydrazides in the presence of BF₃·OEt₂. Most importantly, all BOPAHY dyes show excellent photophysical properties with quantum yields up to 0.92. Steady-state spectroscopy and quantum chemical calculations provide a first insight into these promising properties.

Chemical Communications

BOPAHY: a doubly chelated highly fluorescent pyrrole–acyl hydrazone –BF₂ chromophore†

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BOPAHY: a doubly chelated highly fluorescent pyrrole–acyl hydrazone –BF₂ chromophore

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