alpha-Amino Acid Derived Benzimidazole-Linked Rhodamines: A Case of Substitution Effect at the Amino Acid Site toward Spiro Ring Opening for Selective Sensing of Al3+ Ions

作者：Majumdar Anupam; Mondal Subhendu; Daniliuc Constantin G; Sahu Debashis; Ganguly Bishwajit^*; Ghosh Sourav; Ghosh Utpal; Ghosh Kumaresh^*

来源：Inorganic Chemistry, 2017, 56(15): 8889-8899.

DOI：10.1021/acs.inorgchem.7b00835

alpha-Amino acid derived benzimidazole-linked rhodamines, have been synthesized, and their Metal ion sensing properties have been evaluated. Experimentally, L-valine- and L-phenylglycine-derived benzimidazole-based rhodamines 1 and 2 selectively recognize Al3+ ion in aqueous CH3CN (CH3CN/H2O 4/1 v/v, 10 mM tris HCl buffer, pH 7.0) over the other cations by exhibiting color and "turn-on" emission changes. In contrast, glycine-derived benzimidazole 3 remains silent in the recognition event and emphasizes the role of alpha-substitution of amino acid undertaken in the design. The fact has been addressed on the basis of the single-crystal X-ray structures and theoretical calculations. Moreover, pink 1.Al3+ and 2.Al3+ ensembles selectively sensed F- ions over other halides through a discharge of color. Importantly, compounds 1 and 2 are cell permeable and have been used as imaging reagents for the detection of Al3+ uptake in human lung carcinoma cell line A549.

• 出版日期2017-8-7
• 单位海洋化工研究院有限公司