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From simple Katritzky salts to AIEgens: mechanochromic luminescence and heparin detection
Materials Chemistry Frontiers ( IF 7 ) Pub Date : 2020-03-18 , DOI: 10.1039/c9qm00783k
Faxu Lin 1, 2, 3, 4, 5 , Yang Feng 1, 2, 3, 4, 5 , Xiaoqing Liu 6, 7, 8, 9 , Lei Wang 1, 2, 3, 4, 5 , Zhen-Qiang Yu 4, 5, 9, 10, 11 , Yi Liu 1, 2, 3, 4, 5
Affiliation  

Developing and exploring efficient fluorophores are of fundamental significance for sensing and tracking chemical or biological species and processes. Herein, a series of novel AIEgens derived from Katritzky pyridinium salts have been readily synthesized via a condensation reaction between their corresponding pyrylium precursors and versatile primary amines such as alkylamine and amino acid derivatives. The model compound TPP1 with a 2,4,6-triphenylpyridinium skeleton showed a smooth AIE curve without an inflection point, and the emission enhancement was attributed to the formation of water clusters around the pyridinium ring and the subsequent nano-aggregate formation, which hindered their intramolecular motions. Moreover, tetraphenylethene moiety-conjugated Katritzky salts retained classical AIE properties and were endowed with larger Stokes shifts and red-shifted emissions. Moreover, all these cationic AIE-active chromophores exhibited obvious mechanofluorochromism behaviors with red-shifted luminescence upon grinding and blue-shifted emission after solvent annealing. The existence of the positively charged pyridinium ring endowed these luminogens with the capability to selectively detect Heparin in aqueous media from other ionic biopolymers.

中文翻译:

从简单的Katritzky盐到AIEgens:机械变色发光和肝素检测

开发和探索有效的荧光团对于感测和跟踪化学或生物物种和过程具有根本意义。在此,通过其相应的吡啶鎓前体与通用的伯胺如烷基胺和氨基酸衍生物之间的缩合反应,已经容易地合成了衍生自卡特里茨基吡啶鎓盐的一系列新型AIEgen 。模型化合物TPP1具有2,4,6-三苯基吡啶鎓骨架的分子显示出平滑的AIE曲线而没有拐点,并且发射增强归因于吡啶鎓环周围水簇的形成以及随后的纳米聚集体形成,这阻碍了它们的分子内运动。此外,四苯基乙烯部分共轭的Katritzky盐保留了经典的AIE特性,并具有更大的斯托克斯位移和红移排放。此外,所有这些阳离子AIE活性发色团均表现出明显的机械氟致变色行为,在研磨时发生红移发光,在溶剂退火后发生蓝移发光。带正电的吡啶鎓环的存在使这些发光剂能够选择性地从其他离子生物聚合物中检测水性介质中的肝素。
更新日期:2020-03-18
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