An AIE-active hemicyanine fluorogen with stimuli-responsive red/blue emission: extending the pH sensing range by "switch+knob" effect

被引：171

作者：

Chen, Sijie ^{[1
,5
]}

Liu, Jianzhao ^{[2
,3
,5
,6
]}

Liu, Yang ^{[2
,3
]}

Su, Huimin ^{[4
]}

Hong, Yuning ^{[2
,3
,5
]}

Jim, Cathy K. W. ^{[2
,3
,5
,6
]}

Kwok, Ryan T. K. ^{[2
,3
,5
,6
]}

Zhao, Na ^{[2
,3
,5
,6
]}

Qin, Wei ^{[2
,3
,5
,6
]}

Lam, Jacky W. Y. ^{[2
,3
,5
,6
]}

Wong, Kam Sing ^{[4
]}

Tang, Ben Zhong ^{[1
,2
,3
,5
,6
,7
]}

机构：

[1] HKUST, Div Biomed Engn, Kowloon, Hong Kong, Peoples R China

[2] HKUST, Dept Chem, Kowloon, Hong Kong, Peoples R China

[3] HKUST, Inst Mol Funct Mat, Kowloon, Hong Kong, Peoples R China

[4] HKUST, Dept Phys, Kowloon, Hong Kong, Peoples R China

[5] HKUST, State Key Lab Mol Neurosci, Kowloon, Hong Kong, Peoples R China

[6] HKUST Fok Ying Tung Res Inst, Guangzhou, Guangdong, Peoples R China

[7] Zhejiang Univ, Dept Polymer Sci & Engn, Hangzhou 310027, Peoples R China

来源：

CHEMICAL SCIENCE | 2012年 / 3卷 / 06期

基金：

美国国家科学基金会;

关键词：

AGGREGATION-INDUCED EMISSION; EFFICIENT LIGHT EMITTERS; STEREOSELECTIVE-SYNTHESIS; CYANINE DYES; INDICATORS; DESIGN;

D O I：

10.1039/c2sc01108e

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

In this work, a red-emissive zwitterionic hemicyanine dye, named TPE-Cy, containing tetraphenylethene (TPE) and N-alkylated indolium is designed and synthesized. TPE-Cy inherits the aggregation-induced emission (AIE) feature of TPE and displays a large Stokes shift (>185 nm), overcoming the limitations of the concentration-quenching effect and small Stokes shift (from a few to 20 nm) encountered by conventional cyanine dyes. By taking advantage of the photophysical AIE property and chemical reactivity towards OH-/H+, TPE-Cy is able to sense pH in a broad range (the broadest to date) by showing different emission colors and intensities: strong to moderate red emission at pH 5-7, weak to no emission at pH 7-10, and no emission to strong blue emission at pH 10-14. The acid/base-switched red/blue emission transition is reversible and can be repeated for many cycles. By means of NMR and HRMS analyses, we have drawn a mechanistic picture at molecular level to illustrate how this dye works as a pH-sensitive fluorescent probe.

引用

页码：1804 / 1809

页数：6

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