基于噻吩并噻吩的给-受体型荧光材料性能研究—–用于酸碱响应的荧光编码
PDF下载 (64)刘会敏,陈 斌.基于噻吩并噻吩的给-受体型荧光材料性能研究—–用于酸碱响应的荧光编码[J].宁波大学学报(理工版),2026,39(1):50-57.DOI:10.20098/j.cnki.1001-5132.2025.0121
LIU Huimin,CHEN Bin.Study on the properties of donor-acceptor type luminogens derived from thieno[3,2-b]thiophene: fluorescence encoding for acid-base response[J].Journal of Ningbo University(Natural Science & Engineering Edition),2026,39(1):50-57.DOI:10.20098/j.cnki.1001-5132.2025.0121
| Title: | Study on the properties of donor-acceptor type luminogens derived from thieno[3,2-b]thiophene: fluorescence encoding for acid-base response |
| 作者: | 刘会敏, 陈 斌 |
| Author(s): | LIU Huimin, CHEN Bin |
| 关键词: | 稠环噻吩; 噻吩并[3,2-b]噻吩; 酸碱刺激响应; 荧光编码 |
| Keywords: | fused thiophene; thieno[3,2-b]thiophene; acid-base stimulus response; fluorescence coding |
| 分类号: | O626.12 |
| DOI: | 10.20098/j.cnki.1001-5132.2025.0121 |
| 文献标识码: | A |
| 摘要: | 刺激响应性荧光材料因具备荧光发射随外部环境改变而变化的特性，已被广泛应用于信息防伪、生物成像和荧光传感器等领域，因此本文采用富电子的噻吩并[3,2-b]噻吩（TT）为核心，引入吡啶基团和具有强给电子能力的三苯胺等作为修饰基团，设计合成了给-受体（Donor-Acceptor）结构的荧光材料，并将其应用于酸碱响应的荧光编码。新型分子的合成为细胞内肿瘤微酸碱环境的监测、信息防伪和荧光编码等领域提供了新的分子设计思路。 |
| Abstract: | Stimuli-responsive fluorescent materials possess the characteristic that their fluorescence emission changes with alterations in the external environment. They are widely applied in information anti-counterfeiting, biological imaging, and fluorescence sensors, etc. Therefore, based on the electron-rich thieno[3,2-b]thiophene (TT) core, by introducing pyridyl groups and triphenylamine with strong electron-donating ability as modifying groups, a fluorescent material with donor-acceptor structure was designed and synthesized, and was applied in acid-base responsive fluorescence coding. The synthesis of new molecules provides new molecular design ideas for monitoring the intracellular tumor micro-acid-base environment, information anti-counterfeiting, and fluorescence coding, among others. |
| 参考文献 /References: | [1].BENSON C R, KACENAUSKAITE L, VANDEN- BURGH K L, et al. Plug-and-play optical materials from fluorescent dyes and macrocycles[J]. Chem, 2020, 6(8): 1978-1997. [2].ZHU H, LI Q, ZHU W J, et al. Pillararenes as versatile building blocks for fluorescent materials[J]. Accounts of materials research, 2022, 3(6):658-668. [3].CHANG M J, CHEN W N, XUE H D, et al. Conjugation- extended viologens with thiophene derivative bridges: near-infrared electrochromism, electrofluorochromism, and smart window applications[J]. Journal of materials chemistry C, 2020, 8(45):16129-16142. [4].JONES A L, SCHANZE K S. Fluorescent charge- transfer excited states in acceptor derivatized thiophene oligomers[J]. The journal of physical chemistry A, 2020, 124(35):7001-7013. [5].PAREDIS S, CARDEYNAELS T, DECKERS J, et al. Bridge control of photophysical properties in benzothiazole-phenoxazine emitters-from thermally activated delayed fluorescence to room temperature phosphorescence[J]. Journal of materials chemistry C, 2022, 10(12):4775-4784. [6].CINAR M E, OZTURK T. Thienothiophenes, dithieno- thiophenes, and thienoacenes: syntheses, oligomers, polymers, and properties[J]. Chemical reviews, 2015, 115(9):3036-3140. [7].ISCI R, TEKIN E, KAYA K, et al. Tetraphenylethylene substituted thienothiophene and dithienothiophene derivatives: synthesis, optical properties and OLED applications[J]. Journal of materials chemistry C, 2020, 8(23):7908-7915. [8].ZHOU B J, DAI T T, ZHOU J L, et al. Conjugated D-π-A photovoltaic polymers containing thieno[3,2-b]thiophene π-bridge[J]. Materials chemistry frontiers, 2024, 8(6): 1563-1590. [9].RAFIQ A, ASLAM S, AHMAD M, et al. Recent synthetic approaches towards thienothiophenes: a potential template for biologically active compounds[J]. Molecular diversity, 2024, 28(3):1793-1821. [10].WANG K, OU X W, NIU X F, et al. Aggregation-induced circularly polarized luminescence and delayed fluorescence enabled by activating high-level reverse intersystem crossing[J]. Aggregate, 2025, 6(1):e667. [11].WANG H S, WANG Y, ZHENG Z H, et al. Reasonable design of NIR AIEgens for fluorescence imaging and effective photothermal/photodynamic cancer therapy[J]. Journal of materials chemistry B, 2022, 10(9):1418- 1426. [12].ZHANG C H, LI M, LIANG W D, et al. Substituent effect on the properties of pH fluorescence probes containing pyridine group[J]. ChemistrySelect, 2019, 4(19):5735-5739. [13].龚家亮, 赵树杨, 郭星星, 等. 刺激响应荧光材料研究进展[J]. 广东化工, 2019, 46(6):117-118, 131. [14].YUNYAEVA O, HEAN D E, WOLF M O. Restricted rotation and tunable fluorescence in atropisomeric naphthyl pyridine chromophores[J]. Organic & biomolecular chemistry, 2023, 21(48):9623-9629. [15].ZHANG S N, HUANG M M, LU H, et al. Three-arm star-shaped aniline derivatives: tunable photolumine- scence, aggregation-induced emission and reversible acid-base vapor fluorescence response[J]. Journal of photochemistry and photobiology A: chemistry, 2022, 432:114098. [16].ZHANG S W, LI D, WANG X Y, et al. Aggregation- induced emission properties of pyridyl-containing tetra- arylethenes[J]. Luminescence, 2021, 64(3):958-963. [17].JI H W, CHEN H H, MAO T Z, et al. Encryption- decryption strategy of high security constructed via encoded fluorescence sensing and linear discriminant analysis technique[J]. Advanced optical materials, 2023, 11(23):2300991. [18].NAGARKAR A A, ROOT S E, FINK M J, et al. Storing and reading information in mixtures of fluorescent molecules[J]. ACS central science, 2021, 7(10):1728- 1735. [19].MA J L, DONG Y W, YU Z, et al. A pyridine based Schiff base as a selective and sensitive fluorescent probe for cadmium ions with “turn-on” fluorescence responses [J]. New journal of chemistry, 2022, 46(7):3348-3357. [20].DIXIT M K, MUKHERJEE M, SAHU B K, et al. Dual responsive fluorescence switching of organohydrogel towards base/acid[J]. Molecular systems design & engineering, 2024, 9(12):1210-1214. [21].FENG X J, TIAN P Z, XU Z, et al. Fluorescence- enhanced chemosensor for metal cation detection based on pyridine and carbazole[J]. The journal of organic chemistry, 2013, 78(22):11318-11325. [22].GAYATHRI P, RAVI S, KARTHIKEYAN S, et al. Pyridine nitrogen position controlled molecular packing and stimuli-responsive solid-state fluorescence switching: supramolecular complexation facilitated turn-on fluore- scence[J]. CrystEngComm, 2022, 24(14):2642-2649. [23].ISCI R, RAHIMI VARZEGHANI A, KAYA K, et al. Triphenylamine/tetraphenylethylene substituted 4-thieno [3,2-b]thiophen-3-ylbenzonitriles: synthesis, photophy- sical-electronic properties, and applications[J]. ACS sustainable chemistry & engineering, 2022, 10(4):1605- 1615. |
| 备注/Memo: | 收稿日期：2025-01-17 宁波大学学报（理工版）网址：http://journallg.nbu.edu.cn/ 基金项目：国家自然科学基金（22205120） 第一作者：刘会敏，硕士研究生，主要研究方向为有机发光材料。E-mail: liuhuimin_0407@163.com *通信作者：陈 斌，副研究员，主要研究方向为有机发光材料。E-mail: chenbin2@nbu.edu.cn 宁波大学学报（理工版）网址：http://journallg.nbu.edu.cn/ |
