Photosciences and Photonics Group, Chemical Sciences and Technology Division, National Institute for Interdisciplinary Science and Technology (NIIST), CSIR, Trivandrum-695019, Kerala, India.
Photochem Photobiol Sci. 2012 Nov;11(11):1715-23. doi: 10.1039/c2pp25110h.
The excited state intra molecular charge transfer (ICT) property of fluorophores has been extensively used for the design of fluorescent chemosensors. Herein, we report the synthesis and properties of three donor–π-acceptor–π-donor (D–π-A–π-D) based molecular probes BP, BT and BA. Two heteroaromatic rings, pyrrole (BP), and thiophene (BT) and a non-heteroaromatic ring N-alkoxy aniline (BA) were selected as donor moieties which were linked to a bipyridine binding site through a vinylic linkage. The heteroaromatic systems BP and BT perform selective and ratiometric emission signalling for zinc ions whereas the non-heteroaromatic probe BA does not. The advantages of the D–π-A–π-D design strategy in the design of ICT based probes for the selective fluorescent ratiometric signalling of zinc ions in biological media is discussed. Further, the use of BP, BT and BA for imaging Zn(2+) ions from MCF-7 cell lines is demonstrated.
荧光团的激发态分子内电荷转移（ICT）性质已被广泛用于荧光化学传感器的设计。本文报道了三种基于给体-π-受体-π-给体（D-π-A-π-D）的分子探针 BP、BT 和 BA 的合成及性质。吡咯（BP）和噻吩（BT）两种杂环以及非杂环 N-烷氧基苯胺（BA）被选为供体部分，通过乙烯基键连接到联吡啶结合位点上。杂芳烃 BP 和 BT 对锌离子表现出选择性和比率型发射信号，而非杂芳烃探针 BA 则没有。讨论了 D-π-A-π-D 设计策略在设计 ICT 基探针用于生物介质中锌离子选择性荧光比率信号方面的优势。此外，还展示了 BP、BT 和 BA 用于 MCF-7 细胞系中 Zn(2+) 离子成像的应用。
