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There has been tremendous interest in photo-induced charge transfer phenomena because the process can be initiated at a well defined instant and spectroscopic investigations can monitor the changes easily. The present work deals with a systematic study on the ICT behavior of two different cinnamic acid derivatives in different media. Despite potential complexity of microaggregates containing intrinsically heterogeneous systems, several mean microscopic properties were obtained using fluorimetric titration. The applicability of ICT fluorescence of these probes to characterize different known micro-heterogeneous systems point towards designing efficient fluorescence based polarity sensors. The present work can be extended to understand the aggregation behavior and structure of the microenvironments of newly developed synthetic detergents. The present work is intended to serve as a handy reference to the graduate & research students as well as professionals perusing the work in the field of ICT fluorescence to probe different bio-mimicking systems.