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Linkage between Fluorescence and Electrochemical Properties of Imidazolium Compounds in Acetonitrile Solution
Author(s) -
VillaseñorGranados Tayde O.,
RodríguezLópez Germán,
RamosGarcía Iris,
MoralesMartínez Daniel,
González Felipe J.,
FloresParra Angelina
Publication year - 2020
Publication title -
chemphyschem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.016
H-Index - 140
eISSN - 1439-7641
pISSN - 1439-4235
DOI - 10.1002/cphc.202000128
Subject(s) - acetonitrile , chemistry , reactivity (psychology) , electron transfer , fluorescence , electrochemistry , chloride , stacking , ring (chemistry) , molecule , photochemistry , organic chemistry , electrode , medicine , physics , alternative medicine , pathology , quantum mechanics
The fluorescence properties of some imidazolium derivatives are relevant in photosensing and therefore, the structural analysis of them is a key point for its rational design, which would be useful to prepare new systems with novel applications. Herein we report a multidisciplinary study of the fluorescence and voltammetric properties of three imidazolium compounds {1,3‐bis[(R,R)‐1′‐chloro‐1′‐phenylpropan‐2′‐yl]‐imidazolium chloride ( 1 ), 1,3‐bis[(Z)‐1′‐phenylprop‐1′‐en‐2′‐yl]imidazolium chloride ( 2 ) 1,3‐bis[(R)‐1′‐chlorobutan‐2′‐yl]‐imidazolium chloride ( 3 )}. Electronic structure calculations and Bader analyses were used to correlate both fluorescence and the capability of the molecules to be reduced through a heterogeneous electron transfer process. Both properties are strongly dependent on the proton in position two of the imidazolium ring, where the electron transfer as well as the excitation of the electrons are carried out. The reactivity in this position is controlled by the N‐substituents on the imidazolium ring and is due to single contacts H⋅⋅⋅Cl − , tricentric contacts Cl⋅⋅⋅Cl − ⋅⋅⋅Cl, π‐electronic delocalization and π‐stacking interactions.