Multiple hydrogen bonds tuning guest/host excited-state proton transfer reaction: its application in molecular recognition |
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Authors: | Chou He-Chun Hsu Chin-Hao Cheng Yi-Ming Cheng Chung-Chih Liu Hsiao-Wei Pu Shih-Chieh Chou Pi-Tai |
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Institution: | Department of Chemistry, National Taiwan University, No. 1, Sec. 4, Roosevelt Road, Taipei, Taiwan, R.O.C. |
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Abstract: | A molecular recognition concept exploiting multiple-hydrogen-bond fine-tuned excited-state proton-transfer (ESPT) was conveyed using 3,4,5,6-tetrahydrobis(pyrido3,2-g]indolo)2,3-a:3',2'-j]acridine (1a). The catalytic type 1a/carboxylic acids hydrogen-bonding (HB) complexes undergo ultrafast ESPT, resulting in an anomalously large Stokes shifted tautomer emission (lambdamax approximately 600 nm). Albeit forming a quadruple HB complex, ESPT is prohibited in the noncatalytic-type 1a/urea complexes (lambdamax approximately 430 nm). The HB configuration tuning ESPT properties lead to a feasible design for sensing multiple-HB-site analytes of biological interest. |
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