School of Chemistry and Chemical Engineering, University of Chinese Academy of Sciences , Beijing 100049, P. R. China.
College of Materials Science and Optoelectronic Technology, University of Chinese Academy of Sciences , Beijing 100049, P. R. China.
ACS Appl Mater Interfaces. 2017 Apr 26;9(16):13920-13927. doi: 10.1021/acsami.7b02013. Epub 2017 Apr 17.
A new type of phosgene probe with a limit of detection down to 0.12 nM, response time of less than 1.5 s, and high selectivity over other similarly reactive toxic chemicals was developed using ethylenediamine as the recognition moiety and 8-substituted BODIPY unit as the fluorescence signaling component. The probe undergoes sequential phosgene-mediated nucleophilic substitution reaction and intramolecular cyclization reaction with high rate, yielding a product with the intramolecular charge transfer (ICT) process from amine to the BODIPY core significantly inhibited. Owing to the emission feature of 8-substituted BODIPY that is highly sensitive to the substituent's electronic nature, such inhibition on the ICT process strikingly generates strong fluorescence contrast by a factor of more than 23 300, and therefore creates the superhigh sensitivity of the probe for phosgene. Owing to the high reactivity of ethylenediamine of the probe in nucleophilic substitution reactions, the probe displays a very fast response rate to phosgene.
一种新型的光气探针，其检测限低至 0.12 nM，响应时间小于 1.5 s，对其他类似反应性的有毒化学物质具有很高的选择性，它使用乙二胺作为识别部分和 8-取代的 BODIPY 单元作为荧光信号组件。探针经历连续的光气介导的亲核取代反应和分子内环化反应，具有很高的速率，生成的产物具有从胺到 BODIPY 核心的分子内电荷转移（ICT）过程显著抑制。由于 8-取代的 BODIPY 的发射特征对取代基的电子性质非常敏感，因此，这种 ICT 过程的抑制会产生超过 23300 倍的强烈荧光对比，从而为探针对光气的超高灵敏度创造了条件。由于探针中乙二胺的高反应性，探针对光气表现出非常快的响应速度。
