jo8b00770_si_002.pdf (3.92 MB)
Fluorescence of Cyclopropenium Ion Derivatives
journal contribution
posted on 2018-05-23, 00:00 authored by Lee Belding, Matt Guest, Richard Le Sueur, Travis DuddingThe
synthesis of cyclopropenium-substituted amino compounds and
analysis of their photophysical properties is described. Systematic
structural modifications of these derivatives lead to measurable and
predictable changes in molar extinction coefficients, quantum yields,
and Stokes shifts. Using time-dependent density functional theory
(TD-DFT) calculations, the origin of these trends was traced to internal
charge transfer (ICT) coupled with ensuing structural reorganization
for select naphthalene functionalized derivatives. Associated with
this structural reorganization was an inward gearing of the cyclopropenium
ring and twisting of the peri-NMe2 group
into coplanarity with the naphthalene ring system. Further, reinforcement
of an intramolecular H-bond (IMHB) in the excited state of these derivatives
alludes to the importance of photoinduced H-bonding in this new
class of cyclopropenium based fluorophores.
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naphthalene functionalized derivativescyclopropenium ringphotophysical propertiesintramolecular H-bondquantum yieldstime-dependent densityCyclopropenium Ion DerivativesNMe 2 groupcharge transfernaphthalene ring systemICTStokes shiftsreorganizationmolar extinction coefficientsTD-DFTphotoinduced H-bondingIMHB
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