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 - Funding Information:
Financial support for this work from Pennsylvania State University is acknowledged. This computational research was also supported in part by the National Science Foundation through XSEDE resources, provided by San Diego Supercomputing Center, under grant number TG-CHE160074.
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 -