Mingguang Zhu , Jinghui Zeng , Xinyu Ye , Jiali Hu , Yuanbin Wu , Meihui Chen , Donghong Xie , Huihua Gong , Zhenye Wang , Liu Yang , Yaohui You
{"title":"一种新型水杨醛席夫碱功能化1,8-萘酰亚胺发光团，具有可控制的聚集/固体/膜荧光和可逆的酸/碱刺激响应膜荧光","authors":"Mingguang Zhu , Jinghui Zeng , Xinyu Ye , Jiali Hu , Yuanbin Wu , Meihui Chen , Donghong Xie , Huihua Gong , Zhenye Wang , Liu Yang , Yaohui You","doi":"10.1016/j.molstruc.2025.141888","DOIUrl":null,"url":null,"abstract":"<div><div>In the quest to engineer multifunctional fluorescent materials, 1,8-naphthalimide (NPI) and salicylaldehyde Schiff base molecules were considered as the promising fluorophores because of their fascinating vistas. Herein, from 1,8-naphthalic anhydride precursor, a novel salicylaldehyde Schiff-base-functionalized 1,8-naphthalimide (NPI) luminophore, where NPI core and salicylaldehyde Schiff base were judiciously integrated through a flexible methylene spacer, was elaborately designed and successfully synthesized in a high yield of 90 %. The structure-property relationship was meticulously lucubrated by comparing the photophysical properties of it and its analogues. Mainly, it enjoyed excited-state intramolecular proton transfer (ESIPT) process upon photoexcitation in solution state. Interestingly, it showed the vividly fluorochromic behaviours at the unimolecular level in the aggregation/solid/film states. Specifically, it exhibited multiple self-assembly stages in the proportionally mixed solutions of THF/H<sub>2</sub>O with different water fractions (<em>f</em><sub>w</sub>), accompanying fluorescence transitions from aggregation-induced emission (AIE)+ESIPT-based emission to <em>J</em>-type aggregation-induced emission to H-type aggregation caused quenching. Moreover, its film fabricated by casting EtOH solution (10<sup>−5</sup> M) onto the glass slide displayed thickness-dependent fluorescence colour changes and reversible acid/base stimuli-responsive fluorescence. Furthermore, its solid obtained by crystallization in the EtOH/water (1/1, v/v) mixtures (approximately 10<sup>−2</sup> M) exhibited the reversible mechanochromic luminescence. This work not only realized efficient and controllable aggregation/solid/film fluorescence from a salicylaldehyde Schiff-base-functionalized 1,8-naphthalimide luminophore but also provided a strategy for constructing NPI-based smart fluorescent materials.</div></div>","PeriodicalId":16414,"journal":{"name":"Journal of Molecular Structure","volume":"1334 ","pages":"Article 141888"},"PeriodicalIF":4.7000,"publicationDate":"2025-07-05","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"A novel salicylaldehyde Schiff-base-functionalized 1,8-naphthalimide luminophore with controllable aggregation/solid/film fluorescence and reversible acid/base stimuli-responsive film fluorescence\",\"authors\":\"Mingguang Zhu , Jinghui Zeng , Xinyu Ye , Jiali Hu , Yuanbin Wu , Meihui Chen , Donghong Xie , Huihua Gong , Zhenye Wang , Liu Yang , Yaohui You\",\"doi\":\"10.1016/j.molstruc.2025.141888\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<div><div>In the quest to engineer multifunctional fluorescent materials, 1,8-naphthalimide (NPI) and salicylaldehyde Schiff base molecules were considered as the promising fluorophores because of their fascinating vistas. Herein, from 1,8-naphthalic anhydride precursor, a novel salicylaldehyde Schiff-base-functionalized 1,8-naphthalimide (NPI) luminophore, where NPI core and salicylaldehyde Schiff base were judiciously integrated through a flexible methylene spacer, was elaborately designed and successfully synthesized in a high yield of 90 %. The structure-property relationship was meticulously lucubrated by comparing the photophysical properties of it and its analogues. Mainly, it enjoyed excited-state intramolecular proton transfer (ESIPT) process upon photoexcitation in solution state. Interestingly, it showed the vividly fluorochromic behaviours at the unimolecular level in the aggregation/solid/film states. Specifically, it exhibited multiple self-assembly stages in the proportionally mixed solutions of THF/H<sub>2</sub>O with different water fractions (<em>f</em><sub>w</sub>), accompanying fluorescence transitions from aggregation-induced emission (AIE)+ESIPT-based emission to <em>J</em>-type aggregation-induced emission to H-type aggregation caused quenching. Moreover, its film fabricated by casting EtOH solution (10<sup>−5</sup> M) onto the glass slide displayed thickness-dependent fluorescence colour changes and reversible acid/base stimuli-responsive fluorescence. Furthermore, its solid obtained by crystallization in the EtOH/water (1/1, v/v) mixtures (approximately 10<sup>−2</sup> M) exhibited the reversible mechanochromic luminescence. This work not only realized efficient and controllable aggregation/solid/film fluorescence from a salicylaldehyde Schiff-base-functionalized 1,8-naphthalimide luminophore but also provided a strategy for constructing NPI-based smart fluorescent materials.</div></div>\",\"PeriodicalId\":16414,\"journal\":{\"name\":\"Journal of Molecular Structure\",\"volume\":\"1334 \",\"pages\":\"Article 141888\"},\"PeriodicalIF\":4.7000,\"publicationDate\":\"2025-07-05\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Journal of Molecular Structure\",\"FirstCategoryId\":\"92\",\"ListUrlMain\":\"https://www.sciencedirect.com/science/article/pii/S0022286025005745\",\"RegionNum\":2,\"RegionCategory\":\"化学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"2025/2/27 0:00:00\",\"PubModel\":\"Epub\",\"JCR\":\"Q2\",\"JCRName\":\"CHEMISTRY, PHYSICAL\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Journal of Molecular Structure","FirstCategoryId":"92","ListUrlMain":"https://www.sciencedirect.com/science/article/pii/S0022286025005745","RegionNum":2,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"2025/2/27 0:00:00","PubModel":"Epub","JCR":"Q2","JCRName":"CHEMISTRY, PHYSICAL","Score":null,"Total":0}
A novel salicylaldehyde Schiff-base-functionalized 1,8-naphthalimide luminophore with controllable aggregation/solid/film fluorescence and reversible acid/base stimuli-responsive film fluorescence
In the quest to engineer multifunctional fluorescent materials, 1,8-naphthalimide (NPI) and salicylaldehyde Schiff base molecules were considered as the promising fluorophores because of their fascinating vistas. Herein, from 1,8-naphthalic anhydride precursor, a novel salicylaldehyde Schiff-base-functionalized 1,8-naphthalimide (NPI) luminophore, where NPI core and salicylaldehyde Schiff base were judiciously integrated through a flexible methylene spacer, was elaborately designed and successfully synthesized in a high yield of 90 %. The structure-property relationship was meticulously lucubrated by comparing the photophysical properties of it and its analogues. Mainly, it enjoyed excited-state intramolecular proton transfer (ESIPT) process upon photoexcitation in solution state. Interestingly, it showed the vividly fluorochromic behaviours at the unimolecular level in the aggregation/solid/film states. Specifically, it exhibited multiple self-assembly stages in the proportionally mixed solutions of THF/H2O with different water fractions (fw), accompanying fluorescence transitions from aggregation-induced emission (AIE)+ESIPT-based emission to J-type aggregation-induced emission to H-type aggregation caused quenching. Moreover, its film fabricated by casting EtOH solution (10−5 M) onto the glass slide displayed thickness-dependent fluorescence colour changes and reversible acid/base stimuli-responsive fluorescence. Furthermore, its solid obtained by crystallization in the EtOH/water (1/1, v/v) mixtures (approximately 10−2 M) exhibited the reversible mechanochromic luminescence. This work not only realized efficient and controllable aggregation/solid/film fluorescence from a salicylaldehyde Schiff-base-functionalized 1,8-naphthalimide luminophore but also provided a strategy for constructing NPI-based smart fluorescent materials.
期刊介绍：
The Journal of Molecular Structure is dedicated to the publication of full-length articles and review papers, providing important new structural information on all types of chemical species including:
• Stable and unstable molecules in all types of environments (vapour, molecular beam, liquid, solution, liquid crystal, solid state, matrix-isolated, surface-absorbed etc.)
• Chemical intermediates
• Molecules in excited states
• Biological molecules
• Polymers.
The methods used may include any combination of spectroscopic and non-spectroscopic techniques, for example:
• Infrared spectroscopy (mid, far, near)
• Raman spectroscopy and non-linear Raman methods (CARS, etc.)
• Electronic absorption spectroscopy
• Optical rotatory dispersion and circular dichroism
• Fluorescence and phosphorescence techniques
• Electron spectroscopies (PES, XPS), EXAFS, etc.
• Microwave spectroscopy
• Electron diffraction
• NMR and ESR spectroscopies
• Mössbauer spectroscopy
• X-ray crystallography
• Charge Density Analyses
• Computational Studies (supplementing experimental methods)
We encourage publications combining theoretical and experimental approaches. The structural insights gained by the studies should be correlated with the properties, activity and/ or reactivity of the molecule under investigation and the relevance of this molecule and its implications should be discussed.
京公网安备 11010802042870号
京ICP备2023020795号-1
分享
求助内容：
应助结果提醒方式：
扫码关注我们
