TY - JOUR
T1 - Emission pathway switching by solvent polarity
T2 - Facile synthesis of benzofuran-bipyridine derivatives and turn-on fluorescence probe for zinc ions
AU - Jung, Jiyoung
AU - Dinescu, Adriana
N1 - Publisher Copyright:
© 2016 Elsevier Ltd
PY - 2017
Y1 - 2017
N2 - 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.
AB - 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.
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U2 - 10.1016/j.tetlet.2016.12.039
DO - 10.1016/j.tetlet.2016.12.039
M3 - Article
AN - SCOPUS:85007486873
SN - 0040-4039
VL - 58
SP - 358
EP - 361
JO - Tetrahedron Letters
JF - Tetrahedron Letters
IS - 4
ER -