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| Monitoring and Cell Imaging of H2S Using an Aggregation Induced Fluorescence Probe Based on Excited Intramolecular Proton Transfer |
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| DOI： |
| KeyWord:H2S ?excited-state intramolecular proton transfer （ESIPT） ?aggregation-induced emission （AIE） ?food samples ?cell imaging |
| Author | Institution |
| LIU Fu-rong，YAN Li，FAN Zhe-feng，WEN Xiao-ye |
College of Chemistry and Materials Science，Shanxi Normal University，Taiyuan ，China |
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| Abstract: |
| As one endogenous gas in organisms，abnormal H2S is critically involved in various diseases and pathology research．Hence，high-sensitivity and high-selectivity methods for real-time monitoring of H2S molecule level?in vivo are significantly demanded．In this paper，given the excellent performances of aggregation and enhanced fluorescence，aggregation-induced emission（AIE） fluorescence molecular in the field of biological imaging，a high-efficiency and novel probe 1 based AIE was synthesized via one-step method with 4-acetamidobenzaldehyde and carbohydrazide．The AIE characteristic，luminescence mechanism and sensing mechanism of the probe 1 were discussed by emission spectrum，ultraviolet spectrum，particle size molecules analysis，scanning electron microscopy and theoretical calculation．The AIE properties of the probe may be attributed to the effects of excited-state intramolecular proton transfer（ESIPT） and restricted intramolecular rotation（RIR）．Given the“alcohol-ketone”tautomerism，the probe molecule mainly exists in the keto form mediated by intramolecular hydrogen bonding between hydroxyl and carbonyl groups in water medium—a poor solvent，which indicates that the ESIPT process is activated．Meanwhile，the intramolecular single bond rotation is hindered and the molecular planarity is enhanced due to the orderly alignment between molecules．These two features both facilitate the radiative pathway，thus resulting in remarkable green-emissive．On the other hand，the probe 1 with Schiff base structure can specififically bind with Cu2+．The fluorescence of the probe would be essentially quenched due to the blocked ESIPT．When the probe 1 with Cu2+ is exposed to HS－，the green-emissive could be restored based on the strong binding of HS－ and Cu2+．Herein，a fast and sensitive“turn-on”H2S fluorescent probe was successfully designed．Probe 1 + Cu2+ features a high selectivity towards H2S，after adding HS－ to probe 1 + Cu2+，the fluorescence intensity at 500 nm gradually increases within 30 s and tends to stable．The detection limit of the probe 1 over H2S in containing 10% DMSO solution（PBS buffer，pH 7.4） was 0.27 μmol/L．The outstanding optical properties and biocompatibility made the probe 1 applicable to detecting exogenous H2S concentration in cells and H2S concentration in liquors．The applicability of probe 1 in detecting H2S in liquids，living cells and logic gate programs was further evaluated．The evaluation results showed that the probe is suitable for detecting the concentration of H2S in wine samples，and the probe has very low toxicity．Successfully applied to biofluorescence imaging of exogenous H2S in living cells．In addition，probe 1 was also used to construct an ultra-sensitive logic gate．Importantly，qualitative H2S detection was realized by using commercial filter paper．This research provides a new clue for exploring the functions of H2S in various physiological processes and food samples. |
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