Novel Naphthalimide‐Based Self‐Assembly Systems with Different Terminal Groups for Sensitive Detection of Thionyl Chloride and Oxalyl Chloride in Two Modes

Abstract

AbstractTwo novel naphthalimide derivatives‐based chemosensors with the terminal groups of ethanediamine and 1,3‐diaminopropane (1 and 2) were designed and synthesized. Two compounds exhibited obvious solvatochromism properties. They could respond to some kinds of acyl chlorides through reaction with the ethylenediamine group and propylene diamine group at 4‐site. It was found that they had different response performance due to their different terminal groups. Compound 1 could sensitively detect thionyl chloride (SOCl2) and oxalyl chloride ((COCl)2) with the low limit detection (LOD) of 29.54 nΜ and 151.6 pM in the solution state, respectively. Moreover, film 1 could also respond to the abovementioned acyl chloride gases with LOD of 35.5 and 91.98 ppb, respectively. It was different that compound 2 could selectively detect (COCl)2 with a low LOD of 243.4 pM and 35 ppb for its solution and film state, respectively. NMR and HRMS experiments well demonstrated that the different detection mechanism occurred on two sensors. From this work, it was concluded that the little difference between the terminal reaction sites of naphthalimide greatly affected the detection performance, which would open a window for design functional self‐assembly sensors for acyl chlorides based on naphthalimide derivatives.