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A colorimetric and ratiometric fluorescent sensor for biogenic primary amines based on dicyanovinyl substituted phenanthridine conjugated probe
Dyes and Pigments ( IF 4.1 ) Pub Date : 2020-03-19 , DOI: 10.1016/j.dyepig.2020.108346
Manickam Saravanakumar , Balijapalli Umamahesh , Ramasamy Selvakumar , Jothi Dhanapal , S.K. Ashok kumar , Kulathu Iyer Sathiyanarayanan

Two molecules with an aldehyde donor substituted 4'-(7,8,13,14-tetrahydrodibenzo[a,i]phenanthridin-5-yl)-[1,1′-biphenyl]-4-carbaldehyde (5) and a dicyanovinyl acceptor substituted 2-((4'-(7,8,13,14-tetrahydrodibenzo[a,i]phenanthridin-5-yl)-[1,1′-biphenyl]-4-yl)methylene)malanonitrile (7) were synthesized, and both were applied to remarkable solvatochromism studies. Due to their intramolecular charge transfer (ICT) characteristic, both fluorophores, with a positive solvatochromism effect and emission color, changed from blue to green-orange when the polarity was increased from non-polar hexane to polar acetonitrile solvent. Meanwhile, for compound 5 and 7, aggregation induced emission (AIE) and acidochromism studies have been carried out. The obtained results indicated that compound 5 and 7 exhibited tunable aggregation induced emission and quenching of acidochromism for 7. In this study, we have proposed a new method based on dicyanovinyl substituted phenanthridine moiety of 7 for selective and efficient recognition of biogenic primary amines (BPAs), based on the interaction between amine and the dicyanovinyl-linked phenanthridine moiety of 7. It can be cleaved quickly with significant changes in fluorescence (from orange to blue) that produced 7-imine with induced ratiometric fluorescence. UV–visible/fluorescence spectral titration, NMR, mass spectra and DFT spectroscopic studies were proved by the mechanism of amine sensing. Limit of detections 3.67 nM (DA), 28.3 nM (EDA), 65.3 nM (HA) and 15.8 nM (n-BA) are also obtained for this probe 7 with remarkable ratiometric fluorescence enhancement. Additionally, fluorescence test paper with probe (7) was also fabricated and utilized to detect amines.



中文翻译:

基于双氰基乙烯基取代菲啶共轭探针的生化伯胺比色和比例荧光传感器

两个带有醛供体的分子取代了4'-(7,8,13,14-四氢二苯并[a,i]菲啶基-5-基)-[1,1'-联苯] -4-甲醛(5)和二氰基乙烯基受体取代的2-(((4'-(7,8,13,14-四氢二苯并[a,i]菲蒽基-5-基]-[1,1'-联苯] -4-基)亚甲基)丙二腈(7)合成后,两者均用于显着的溶剂变色研究。由于它们的分子内电荷转移(ICT)特性,当极性从非极性己烷增加到极性乙腈溶剂时,具有正溶剂致变色效应和发射颜色的两种荧光团都从蓝色变为绿色橙色。同时,对于化合物57,已经进行了聚集诱导发射(AIE)和酸致变色的研究。获得的结果表明,化合物57表现出可调节的聚集诱导的发射和对于7的酸致变色的猝灭。在这项研究中,我们已经提出了基于的二氰基取代的菲啶基部分的新方法7为生物伯胺(BPAS),基于胺和的二氰基乙烯基联菲啶基之间的相互作用的选择性,高效的识别7。它可以迅速裂解,产生显着的荧光变化(从橙色到蓝色),产生7-亚胺诱导比例荧光。紫外-可见/荧光光谱滴定,NMR,质谱和DFT光谱学研究均通过胺感测机制得到证明。对于具有显着比例荧光增强的探针7,也获得了3.67 nM(DA),28.3 nM(EDA),65.3 nM(HA)和15.8 nM(n-BA)的检出限。另外,还制作了带有探针(7)的荧光试纸,并用于检测胺。

更新日期:2020-03-20
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