Emission pathway switching by solvent polarity: Facile synthesis of benzofuran-bipyridine derivatives and turn-on fluorescence probe for zinc ions

TETRAHEDRON LETTERS

卷:58

Article

Jung, Jiyoung¹  Dinescu, Adriana² 

[1] Penn State Univ Worthington Scranton, Dunmore, PA 18512 USA

[2] Centenary Univ, Hackettstown, NJ 07840 USA

关键词: Benzofuran;    Bipyridine;    Solvatochromism;    Emission pathway switching;    Turn-ON fluorescence;   

DOI  :  10.1016/j.tetlet.2016.12.039

来源: Elsevier

【 摘 要 】

Bipyridine attached benzofuran derivatives were prepared by the cyclization of alkyne ortho-substituted phenols. Electronically different substituents, N,N-dibutylamino vs tert-butyl group, were attached on benzofuran rings. Depending on the polarity and pH of solvent environment, N,N-dialkylamino group participates in two distinctively different roles in emissive properties, i.e., ICT-type and PET-type behaviors. Upon capturing lone-pair electrons of N,N-dialkylamino groups by protonation, ratiometric blue-shift and complete turn-on behaviors were observed in THF and MeCN solution, respectively. Such peculiar behavior was further utilized to show turn-on sensing of zinc ions. (C) 2016 Elsevier Ltd. All rights reserved.

【 授权许可】

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