羟基-炔点击反应制备具有红移发射的非传统荧光化合物及性能

张红燕, 蒋其民*, 史凌月, 张彤, 蒋必彪*

化工新型材料 ›› 2024, Vol. 52 ›› Issue (1) : 238 -242.

PDF
化工新型材料 ›› 2024, Vol. 52 ›› Issue (1) : 238-242. DOI: 10.19817/j.cnki.issn1006-3536.2024.01.038
开发与应用

羟基-炔点击反应制备具有红移发射的非传统荧光化合物及性能

    张红燕, 蒋其民*, 史凌月, 张彤, 蒋必彪*
作者信息 +

Preparation and properties of unconventional fluorescent compounds with red-shifted emission by hydroxyl-yne click reaction

  • Zhang Hongyan, Jiang Qimin, Shi Lingyue, Zhang Tong, Jiang Bibiao
Author information +
文章历史 +
PDF

摘要

以丙炔酸甲酯为原料,分别与2-二乙基氨基乙醇、N-甲基二乙醇胺和三乙醇胺经常温羟基-炔点击反应在无催化剂和无溶剂条件下制备得到三组含叔胺和乙烯基醚非传统发色团的有机荧光化合物。利用傅里叶红外光谱仪(FT-IR)和核磁共振波谱仪(NMR)确证所得化合物的分子结构。利用紫外-可见分光光度计(UV-Vis)和荧光分光光度计探究了化合物的荧光性能,结果表明:所得三组化合物均表现出浓度增强发光及激发波长依赖荧光特性。以三乙醇胺、N-甲基二乙醇胺和2-二乙氨基乙醇分别反应所得化合物的发射波长依次红移,且其红移程度依赖于化合物的浓度,表现出结构和浓度依赖红移荧光特性。该方法实现了简单调控化合物的结构和浓度得到长波长的非传统有机荧光化合物,这为设计长波长非传统荧光材料提供了新的方法和思路。

Abstract

Three organic fluorescent compounds containing tertiary amines and vinyl ether unconventional chromophores were prepared under catalyst-free and solvent-free conditions by hydroxy-alkyne click reaction of methyl propiolate with 2-diethylaminoethanol,N-methyldiethanolamine and triethanolamine at room temperature,respectively.The structures of the obtained compounds were characterized by Fourier transform infrared spectroscopy (FT-IR) and nuclear magnetic resonance spectroscopy (NMR).The fluorescence properties of the compounds were investigated by ultraviolet-visible spectrophotometer (UV-Vis) and fluorescence spectrophotometer.It was found that the obtained compounds exhibited concentration-enhanced luminescence and excitation-dependent fluorescence properties.The emission wavelengths of the compounds obtained by triethanolamine,N-methyldiethanolamine and 2-diethylaminoethanol were red-shifted in order and the degree of red-shift depended on the concentration,showing the structure- and concentration-dependent red-shifted fluorescence properties.Thus,the unconventional organic fluorescent compounds with long emission wavelength could be obtained by simply regulating the structure and concentration,which provided a new and facile approach and idea for the design of long-wavelength unconventional fluorescent materials.

关键词

点击反应 / 有机荧光化合物 / 非传统发色团 / 红移 / 结构

Key words

click reaction / organic fluorescent compound / unconventional chromophores / red-shift / structure

引用本文

引用格式 ▾
羟基-炔点击反应制备具有红移发射的非传统荧光化合物及性能[J]. 化工新型材料, 2024, 52(1): 238-242 DOI:10.19817/j.cnki.issn1006-3536.2024.01.038

登录浏览全文

4963

注册一个新账户 忘记密码

参考文献

[1] 赵跃智,蔡敏敏,钱妍,等.聚集诱导发光体系:化合物种类、发光机制及其应用[J].化学进展,2013,25(Z1):296-321.
[2] 罗海媛,郑捷,梁水妹,等.四苯乙烯衍生物在有机电致发光材料中的研究进展[J].化工新型材料,2016,44(10):14-16.
[3] Zhang H,Zhao Z,McGonigal P R,et al.Clusterization-triggered emission:uncommon luminescence from common materials[J].Materials Today,2020,32:275-292.
[4] 黄田,汪昭旸,秦安军,等.含非典型性生色团的发光聚合物[J].化学学报,2013,71(7):979-990.
[5] 马思阳,张晓琳,宫蕾,等.基于AIE特性的有机小分子和聚合物的应用进展[J].材料导报,2021,35(S1):566-570.
[6] 陈晓红,王允中,张永明,等.非典型发光化合物的簇聚诱导发光[J].化学进展,2019,31(11):1560-1575.
[7] Chu B,Zhang H,Chen K,et al.Aliphatic polyesters with white-light clusteroluminescence[J].Journal of the American Chemical Society,2022,144(33):15286-15294.
[8] Deng J,Jia H,Xie W,et al.Nontraditional organic/polymeric luminogens with red-shifted fluorescence emissions[J].Macromolecular Chemistry and Physics,2022,223:2100425.
[9] Worch J C,Stubbs C J,Price M J,et al.Click nucleophilic conjugate additions to activated alkynes:exploring thiol-yne,amino-yne,and hydroxyl-yne reactions from (bio) organic to polymer chemistry[J].Chemical Reviews,2021,121(12):6744-6776.
[10] Qiu Z,Han T,Lam J W Y,et al.Recent new methodologies for acetylenic polymers with advanced functionalities[J].Polymer Synthesis Based on Triple-bond Building Blocks,2017,375:1-39.
[11] Yao B,Mei J,Li J,et al.Catalyst-free thiol-yne click polymerization:a powerful and facile tool for preparation of functional poly (vinylene sulfide) s[J].Macromolecules,2014,47(4):1325-1333.
[12] He B,Su H,Bai T,et al.Spontaneous amino-yne click polymerization:a powerful tool toward regio- and stereospecific poly(β-aminoacrylate)s[J].Journal of the American Chemical Society,2017,139(15):5437-5443.
[13] Jiang Q,Zhang Y L,Du Y,et al.Preparation of hyperbranched polymers by oxa-Michael addition polymerization[J].Polymer Chemistry,2020,11(7):1298-1306.
[14] Si H,Wang K,Song B,et al.Organobase-catalysed hydroxyl-yne click polymerization[J].Polymer Chemistry,2020,11(14):2568-2575.
[15] Chu B,Zhang H,Hu L,et al.Altering chain flexibility of aliphatic polyesters for yellow-green clusteroluminescence in 38% quantum yield[J].Angewandte Chemie International Edition,2022,61(6):e202114117.

基金资助

国家自然科学青年基金项目(51903020);江苏省自然科学青年基金项目(BK20190932)

AI Summary AI Mindmap
PDF

634

访问

0

被引

导航
相关文章

AI思维导图

/