posted on 2021-09-07, 15:12authored byFarshid Shahrokhi, Maryam F. Abdollahi, Yuming Zhao
A series
of 1,3,6,8-tetraphenylpyrene (TPPy) derivatives substituted
with redox-active 1,4-dithiafulvenyl (DTF) groups was synthesized
and characterized. The conformational properties of these DTF-TPPys
and their TPPy precursors were assessed by X-ray single-crystal and
nuclear magnetic resonance analyses. Their electronic and redox properties
were examined by ultraviolet–visible absorption, fluorescence,
and cyclic voltammetric analyses. The DTF substitution was found to
strongly modify the absorption, emission, and electrochemical properties,
while detailed effects can be linked to substitution patterns and
alkyl side chains attached to the DTF groups. Furthermore, the DTF-TPPy
derivatives showed sensitivity to acids; in particular, the vinylic
proton of DTF group could undergo efficient proton/deuterium exchange
with D2O in an acidic medium.