Font Size: a A A

Investigate On Expanding Application Of Benzothiadiazole-Tetrazole Photo-triggered Click Reaction And Its Product Properties

Posted on:2022-08-03Degree:MasterType:Thesis
Country:ChinaCandidate:Y S WangFull Text:PDF
GTID:2491306323991389Subject:Inorganic Chemistry
Abstract/Summary:PDF Full Text Request
Photo-triggered click reaction is a fast and efficient reaction using light irradiation,which is very useful in different areas,such as chemical sensors,protein cross-linking and materials science.Benzothiadiazole(BTD)is a fine chromophore,showing diverse luminescence behaviors.Under light irradiation,tetrazole rapidly releases N2 generating the high-active intermediate,which can react with various functional groups,such as chloride ion.In this thesis,we design and synthesize new benzothiadiazoletetrazole compounds as substrates to study their photo-triggered click reactions with chloride ions.This thesis contains two parts as below:1.New compounds BT1 and BT2 facilely react with chloride ions under UV light irradiation.In the further exploration for the potential application of reaction-based chloride ion molecular receptor,BT1 or BT2 showed obvious absorption and photoluminescence(PL)responses with good selectivity and sensitivity.Moreover,in the response of BT1 or BT2 to chloride ions,the surprising PL changes induced by the aggregation of photochemical product(BHcl or BHc2)provide a new platform to design reaction-based chloride ion receptor.2.We synthesized photochemical products(BHcl and BHc2)by photo-triggered click reactions with chloride ions,and studied the mononer luminescence in solution,the aggregate luminescence in solution and the luminescence in crystal.X-ray single crystal diffraction analysis indicates that their structure are planar due to two weak intramolecular hydrogen bonding.Due to the rotation of hydrazonyl chloride,partially twisted intramolecular charge transfer(TICT)state is present in the solution of BHcl or BHc2.When the freshly prepared solution of BHcl or BHc2 was in the dark,the PL signal was blue shifted and changed to a fine-structured one due to intermolecular hydrogen bonding aggregation.In crystal,the photoluminescence of BHcl or BHc2 showed a red shift compared with the monomer luminescence in solution due to the intramolecular hydrogen-bond conformational self-locking.These studies provide a theoretical support for the design and synthesis of a new type of photo-triggered click reaction chloride ion molecular receptor.
Keywords/Search Tags:Benzothiadiazole-tetrazole, Photo-triggered click reaction, Reaction-based chloride ion receptor, Intramolecular hydrogen-bond conformational locking, luminescence redshift in crystal
PDF Full Text Request
Related items