Stimuli-responsive molecules are highly desirable in different scenario such as smart materials,bio-imaging,and environment monitoring.Herein,a series of hetero polycycles which show optical response toward chemical s...Stimuli-responsive molecules are highly desirable in different scenario such as smart materials,bio-imaging,and environment monitoring.Herein,a series of hetero polycycles which show optical response toward chemical stimuli are synthesized from trithiasumanene(TTS).The TTS is transformed into ortho-quinone form,which then undergoes three-component Debus-Radziszewski reaction with aldehydes and ammonia to give oxazole-fused TTS(2-6).The thiophene rings on 3-5 are selectively oxidized to thiophene-S,S-dioxides,affording 3-3O_(2)-5-3O_(2).It is found that the electronic structures of these compounds are governed by the sub-stituents on oxazole moiety and oxidation state of thiophene ring.Moreover,these hetero polycycles exhibit optical response toward different chemical stimuli.Particularly,compounds 6 and 3-3O_(2) can serve as fluorescence detectors for harmful chemicals sulfide ions(S2-/HS-)and aniline,respectively.This work indicates that TTS is a promising precursor for the creation of responsive materials.展开更多
基金This work was supported by the National Key R&D Program of China(No.2017YFA0204903)the National Natural Science Foundation of China(No.21871119).
文摘Stimuli-responsive molecules are highly desirable in different scenario such as smart materials,bio-imaging,and environment monitoring.Herein,a series of hetero polycycles which show optical response toward chemical stimuli are synthesized from trithiasumanene(TTS).The TTS is transformed into ortho-quinone form,which then undergoes three-component Debus-Radziszewski reaction with aldehydes and ammonia to give oxazole-fused TTS(2-6).The thiophene rings on 3-5 are selectively oxidized to thiophene-S,S-dioxides,affording 3-3O_(2)-5-3O_(2).It is found that the electronic structures of these compounds are governed by the sub-stituents on oxazole moiety and oxidation state of thiophene ring.Moreover,these hetero polycycles exhibit optical response toward different chemical stimuli.Particularly,compounds 6 and 3-3O_(2) can serve as fluorescence detectors for harmful chemicals sulfide ions(S2-/HS-)and aniline,respectively.This work indicates that TTS is a promising precursor for the creation of responsive materials.
