TY - JOUR
T1 - The influence of amino substituents on the signal-output, selectivity, and sensitivity of a hydroxyaromatic 1,2,3-triazolyl chemosensor for anions—A structure–property relationship investigation
AU - Ghosh, Debanjana
AU - Landge, Shainaz
AU - Zhu, Lei
AU - Ofulue, Unodinma
AU - Akinsoji, Oluwagbotemi A.
AU - Govan, Richard D.
AU - Ugboya, Aikohi
AU - Hernandez, Vincent
AU - Yates, Kayley
AU - Henderson, Arneshia
AU - Aiken, Karelle S.
N1 - Publisher Copyright:
© 2020 John Wiley & Sons, Ltd.
PY - 2020/10/1
Y1 - 2020/10/1
N2 - The influence of strongly electron donating amino groups on a hydroxyaromatic 1,2,3-triazolyl anion chemosensor was investigated with spectroscopic studies (ultraviolet-visible [UV-vis], fluorescence, and nuclear magnetic resonance [NMR]) and computational analyses. This work focused on 2-, 3- and 4-amino derivatives of the parent molecule, 2-(4-phenyl-1H-1,2,3-triazol-1-yl)phenol (PTP). The effect on signal-output, selectivity, sensitivity, and the mechanism of response was explored. In all cases, the incorporation of the amino group enhances fluorescence during anion detection while retaining key properties (the receptor site, a blue-fluorescent response, and the ability to detect F−, H2PO4−, and AcO−—strongest response to F−). Specifically, sensitivity to F− is impacted by the amino group's location. The 2-amino is most responsive to F−, more than PTP and the other amino regioisomers. Results from this work are important for developing predictive, structure-signal tuning models, which will be used in the targeted design of sensors based on the PTP scaffold.
AB - The influence of strongly electron donating amino groups on a hydroxyaromatic 1,2,3-triazolyl anion chemosensor was investigated with spectroscopic studies (ultraviolet-visible [UV-vis], fluorescence, and nuclear magnetic resonance [NMR]) and computational analyses. This work focused on 2-, 3- and 4-amino derivatives of the parent molecule, 2-(4-phenyl-1H-1,2,3-triazol-1-yl)phenol (PTP). The effect on signal-output, selectivity, sensitivity, and the mechanism of response was explored. In all cases, the incorporation of the amino group enhances fluorescence during anion detection while retaining key properties (the receptor site, a blue-fluorescent response, and the ability to detect F−, H2PO4−, and AcO−—strongest response to F−). Specifically, sensitivity to F− is impacted by the amino group's location. The 2-amino is most responsive to F−, more than PTP and the other amino regioisomers. Results from this work are important for developing predictive, structure-signal tuning models, which will be used in the targeted design of sensors based on the PTP scaffold.
KW - 1,2,3-triazole
KW - chemosensor
KW - electron-donating group
KW - structure–property relationship
UR - http://www.scopus.com/inward/record.url?scp=85085147327&partnerID=8YFLogxK
U2 - 10.1002/poc.4078
DO - 10.1002/poc.4078
M3 - Article
AN - SCOPUS:85085147327
SN - 0894-3230
VL - 33
JO - Journal of Physical Organic Chemistry
JF - Journal of Physical Organic Chemistry
IS - 10
M1 - e4078
ER -