Perylene derivatives as a fluorescent probe for sensing of amines in solution

Abstract

Amines play an important role in many physiological processes in living organisms. The present study explores the use of perylene diimide (PDI) and perylene monoimide (PMI) for the detection of common amines in solution. A systematic investigation using primary, secondary and tertiary amines as electron donors and perylene derivatives as electron acceptors is carried out in solution to understand the molecular interactions. Results from steady-state luminescence spectroscopy suggested that the PDI and PMI interact with the amine derivatives in the excited state, which led to photoinduced electron transfer and fluorescence quenching. Stern-Volmer plots were used to understand the quenching behavior of perylene derivatives in presence of various amines. The bimolecular rate constants of the dynamic quenching have been deduced for PDI, the values are in the range of 1.8 × 109 M−1s−1 for primary amines, 8 × 109 M−1s−1 for tertiary amines and 2.2 × 1010 M−1s−1 for aniline. Similar quenching rate constants for primary, secondary and tertiary amines were also observed for PMI. PDI showed higher selectivity for bulky hydrophobic amines over linear primary amines in solution. Such interactions could be investigated further to understand the response of perylene based sensors for amines.