Intermolecular
interactions impact self-assembly phenomena having
a variety of bio/chemical, physical, and mechanical consequences.
Nevertheless, the underlying mechanisms leading to a controlled stereo-
and chemo-specific aggregation at the molecular level often remain
elusive because of the intrinsically dynamic nature of these processes.
Herein, we describe two 3-styryl coumarin molecular rotors capable
of probing subtle intermolecular interactions controlling the self-assembly
of a small-molecule organogelator. Complementing the characterization
of the gel via circular dichroism and atomic force microscopy, thorough
spectroscopic investigations on these sensors were carried out to
prove their high chemical and spatial affinity toward the 3D supramolecular
network. The results were further supported by molecular dynamics
simulations to reveal further critical insights into the gelator’s
dynamic self-assembly mechanism. These sensors could potentially serve
as templates to study a variety of soft-supramolecular architectures
and the ways in which they assemble.