磺化四苯乙烯荧光染料的合成及其发光性能

doi:10.19398/j.att.202205052

现代纺织技术 ›› 2022, Vol. 30 ›› Issue (6): 133-140.DOI: 10.19398/j.att.202205052

磺化四苯乙烯荧光染料的合成及其发光性能

谢沉着^a, 邵晓莉^a, 赵强强^b, 何瑾馨^b

东华大学,a.化学化工与生物工程学院;b.纺织面料技术教育部重点实验室,上海 201620

收稿日期:2022-05-30 出版日期:2022-11-10 网络出版日期:2022-11-16
通讯作者:赵强强,E-mail: qqzhao@dhu.edu.cn
作者简介:谢沉着(1997—),男,河南平顶山人,硕士研究生,主要从事聚集诱导发光效应方面的研究。
基金资助:
中国博士后科学基金资助项目(2021M690599);中央高校基本科研业务费专项资金资助(2232020G-04)

Synthesis and luminescent properties of sulfonated tetraphenylethylene fluorescent dyes

XIE Chenzhuo^a, SHAO Xiaoli^a, ZHAO Qiangqiang^b, HE Jinxin^b

a. College of Chemistry, Chemical Engineering and Biotechnology; b. Key Laboratory of Textile Science & Technology, Ministry of Education, Donghua University, Shanghai 201620, China

Received:2022-05-30 Published:2022-11-10 Online:2022-11-16

摘要/Abstract

摘要： 为了开发在蛋白质纤维上可应用的新型荧光染料,选用具有聚集诱导发光效应(Aggregation-induced emission, AIE)的四苯乙烯(Tetraphenylethylene, TPE)为原料,以浓硫酸和氯磺酸为磺化试剂合成了四磺化四苯乙烯(TPE-4S)和一磺化四苯乙烯(TPE-1S)荧光染料,探究其聚集诱导发光效应,并研究其对蛋白质纤维的上染性能,分析荧光染料在纤维上的发光性能。结果表明:TPE-4S和TPE-1S具有聚集诱导发光效应。两种荧光染料与酸性染料相似可上染蛋白质纤维,磺酸基的数量影响其在纤维上的最大上染量,TPE-4S在羊毛上的最大上染量可达7.0%;由于染料分子与纤维上氨基的离子键作用,使得上染纤维上的磺化四苯乙烯分子具有发光性能。与普通荧光染料相比,TPE-4S在上染量为5.0%时,发生荧光淬灭,TPE-1S在上染量为6.0%时仍然不会发生荧光淬灭。具有聚集诱导效应的荧光染料能有效克服发光材料荧光淬灭的问题。

关键词: 荧光染料, 聚集诱导发光, 染色性能, 磺化反应, 蛋白质纤维

Abstract: In order to develop the new fluorescent dyes that can be applied to protein fibers, tetrasulfonated tetraphenylethylene(TPE-4S) and monosulfonated tetraphenylene(TPE-1S) fluorescent dyes with aggregation-induced emission(AIE) are synthesized from tetraphenylethylene (TPE) using concentrated sulfuric acid and chlorosulfonic acid as sulfonation reagents. Besides, the AIE was investigated, and the dyeing properties on protein fibers were also studied, while the luminescence properties of fluorescent dyes on fibers were analyzed. The results show that TPE-4S and TPE-1S have aggregation-induced emission effect. In addition, the two fluorescent dyes can dye protein fibers similar to acid dyes. The number of sulfonic acid groups affects the maximum dyeing uptake on the fibers, and the maximum dye uptake of TPE-4S on wool can reach 7.0%. Due to the ionic bond between the dye molecules and the amino groups on the fiber, the sulfonated tetrastyrene molecules on the dyed fibers have luminescent properties. Compared with ordinary fluorescent dyes, TPE-4S has fluorescence quenching when the dye uptake is 5.0%, but TPE-1S still does not have fluorescence quenching when the dye uptake is 6.0%, which provides fluorescent dyes with aggregation-induced emission effect can effectively overcome the problem of fluorescence quenching of luminescent materials.

Key words: fluorescent dyes, AIE, dyeing performance, sulfonation, protein fiber

中图分类号:

TS193.8

谢沉着, 邵晓莉, 赵强强, 何瑾馨. 磺化四苯乙烯荧光染料的合成及其发光性能[J]. 现代纺织技术, 2022, 30(6): 133-140.

XIE Chenzhuo, SHAO Xiaoli, ZHAO Qiangqiang, HE Jinxin. Synthesis and luminescent properties of sulfonated tetraphenylethylene fluorescent dyes[J]. Advanced Textile Technology, 2022, 30(6): 133-140.

参考文献

[1] 左晓玲,吴翀,黄安荣,等.可见光响应的荧光增白剂基多功能光引发体系[J].高等学校化学学报,2020,41(4):811-820.
ZUO Xiaoling, WU Chong, HUANG Anrong, et al. Fluo-rescence whitening agent-based multifunctional photoinitiator system with visible light response [J]. Chemical Research in Chinese Universities, 2020, 41(4): 811-820.
[2] 姜雪琴,刘礼,李昊,等.一种香豆素pH荧光染料的开发及应用[J].分析测试学报,2021,40(9):1342-1347.
JIANG Xueqin, LIU Li, LI Hao, et al. Development and application of a coumarin pH fluorescent dye[J]. Journal of Instrumental Analysis, 2021, 40(9): 1342-1347.
[3] 钟伟婷,王智鑫,王堃,等.纳米纤维素发光材料研究进展[J].复合材料学报,2022,39(1):39-47.
ZHONG Weiting, WANG Zhixin, WANG Kun, et al. Research progress of nanocellulose-based luminescent materials[J]. Acta Materiae Compositae Sinica, 2022, 39(1): 39-47.
[4] 胡海娜,吕丽华,熊小庆,等.适用于纺织荧光染色的染料及其应用进展[J].精细化工,2020,37(6):1125-1135.
HU Haina, LÜ Llihua, XIONG Xiaoqing, et al. Dyes suitable for textile fluorescent dyeing and their application progress [J]. Fine Chemicals, 2020, 37(6): 1125-1135.
[5] 张来新,张丹,董帆.新型荧光化学传感器和荧光探针的合成及应用[J].合成材料老化与应用,2019,48(4):141-145.
ZHANG Laixin, ZHANG Dan, DONG Fan. Syntheses and applications of new fluorescence chemical sensors and fluorescence probes[J]. Aging and Application of Synthetic Materials, 2019, 48(4): 141-145.
[6] CHEN K Q, ZHANG R Y, WABG Z M, et al. Structural modification orientated multifunctional AIE fluorescence probes: Organelles imaging and effective photosensitizer for photodynamic therapy[J]. Advanced Optical Materials, 2020, 8(2): 1901433.
[7] ZHAO W J, LIUZ Y, YU J, et al. Turning on solid-state luminescence by phototriggered subtle molecular conforma-tion variations[J]. Advanced Materials, 2020, 33(2):2006844-2006851.
[8] LI G F, ZHOU Z X, YUAN C, et al. Trackable supramo-lecular fusion: Cage to cage transformation of tetrapheny-lethylene-based metalloassemblies[J]. Angewandte Chemie International Edition, 2020, 59(25): 10013-10017.
[9] 韩鹏博,徐赫,安众福,等.聚集诱导发光[J].化学进展,2022,34(1):1-130.
HAN Pengbo, XU He, AN Zhongfu, et al. Aggregation-induced emission[J]. Progress in Chemistry, 2022, 34(1): 1-130.
[10] 焦雳,祝晨飞,张玉建,等.具有聚集诱导发光性质的力致荧光变色材料的研究进展[J].浙江化工,2021,52(8):26-31.
JIAO Li, ZHU Chenfei, ZHANG Yujian, et al. The research progress of force-induced fluorescent discoloration materials with aggregation-induced luminescence properties[J]. Zhejiang Chemical Industry, 2021, 52(8): 26-31.
[11] 丁伟,程勃雯,王萌,等.基于有机光致变色的聚集诱导发光分子的研究进展[J].有机化学,2022,42(2):363-383.
DING Wei, CHENG Bowen, WANG Meng, et al. Advances in aggregation-induced emisson molecules based on organic photochromism[J].Chinese Journal of Organic Chemistry, 2022,42(2):363-383
[12] JIANG Y M, CHENG Y H, LIU S J, et al. Solid-state intramolecular motions in continuous fibers driven by ambient humidity for fluorescent sensors[J]. National Science Review, 2021, 8(4): 142-153.
[13] OOYAMA Y, SUGINO M, ENOKI T, et al. Aggregation-induced emission(AIE) characteristic of water-soluble tetraphenylethene(TPE) bearing four sulfonate salts[J]. New Journal of Chemistry, 2017, 41(12): 4747-4749.
[14] HU Y B, LAM J, TANG B Z. Recent progress in AIE-active polymers[J]. Chinese journal of polymer science, 2018, 37(4): 289-301.
[15] ZHAO W J, HE Z K, PENG Q, et al. Highly sensitive switching of solid-state luminescence by controlling intersystem crossing[J]. Nature Communications,2018, 9: 3044.

磺化四苯乙烯荧光染料的合成及其发光性能

Synthesis and luminescent properties of sulfonated tetraphenylethylene fluorescent dyes

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