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Rational Design of d-PeT Phenylethynylated-Carbazole Monoboronic Acid Fluorescent Sensors for the Selective Detection of alpha-Hydroxyl Carboxylic Acids and Monosaccharides
Zhang, Xin1; Chi, Lina1; Ji, Shaomin1; Wu, Yubo1; Song, Peng2; Han, Keli2; Guo, Huimin3; James, Tony D.4; Zhao, Jianzhang1
刊名JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
2009-12-02
DOI10.1021/ja9060646
131期:47页:17452-17463
收录类别SCI ; IC
文章类型Article
WOS标题词Science & Technology ; Physical Sciences
类目[WOS]Chemistry, Multidisciplinary
研究领域[WOS]Chemistry
关键词[WOS]PHOTOINDUCED ELECTRON-TRANSFER ; INTRAMOLECULAR CHARGE-TRANSFER ; LARGE STOKES SHIFT ; BORONIC ACID ; PHOTOPHYSICAL PROPERTIES ; MOLECULAR RECOGNITION ; ARTIFICIAL RECEPTORS ; CHIRAL RECOGNITION ; ARYLBORONIC ACIDS ; ANTHRACENE DYAD
英文摘要We have synthesized three new phenylethynylated carbazole boronic acid sensors, which were predicted to display novel d-PeT fluorescence transduction (PeT, photoinduced electron transfer; fluorophore as the electron donor of the electron transfer, ET) by DFT/TDDFT calculations. The d-PeT effect is characterized by a lower background fluorescence at acidic pH than at neutral pH, which is in stark contrast to the normal a-PeT effect (fluorophore as the electron acceptor of the ET) that shows a strong and undesired background fluorescence at acidic pH. Our experimental results confirmed the theoretical predictions and d-PeT was observed for two of the sensors (with p-dimethylaminophenylethynyl substitution at 6- position of the carbazole core). For the third sensor (with phenylethynyl substitution at 6- position of the carbazole core), however, not d-PeT but rather the normal a-PeT was observed. The discrepancy between the DFT/TDDFT calculations and the experimental observations can be rationalized using free energy changes (Rehm-Weller equations) and the rate constants for the ET (k(ET), Marcus equation). These new d-PeT boronic acid sensors show improved photophysical properties compared to the known d-PeT sensor reported previously by us. In particular, the fluorescence transduction efficiency of the new sensors was improved 8-fold when compared to the known d-PeT boronic acid sensors. Novel fluorescence enhancement/reduction was observed for one of the sensors upon binding with mandelic acid or tartaric acid at pH 5.6. The effect of pH as well as the bonding with analytes on the emission of the sensors were rationalized using DFT/TDDFT calculations. We believe that rational sensor design aided by DFT/TDDFT calculations as well as using free energy changes and electron transfer rate constants to study the emission properties of PeT sensors will become an essential tool in the design of new fluorophores or fluorescent sensors with predetermined photophysical properties.
语种英语
WOS记录号WOS:000272207300073
引用统计
文献类型期刊论文
条目标识符http://cas-ir.dicp.ac.cn/handle/321008/141574
专题中国科学院大连化学物理研究所
作者单位1.Dalian Univ Technol, State Key Lab Fine Chem, Sch Chem Engn, Dalian 116012, Peoples R China
2.Chinese Acad Sci, Dalian Inst Chem Phys, State Key Lab Mol React Dynam, Dalian 116023, Peoples R China
3.Dalian Univ Technol, Sch Chem Engn, Dept Chem, Dalian 116012, Peoples R China
4.Univ Bath, Dept Chem, Bath BA2 7AY, Avon, England
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Zhang, Xin,Chi, Lina,Ji, Shaomin,et al. Rational Design of d-PeT Phenylethynylated-Carbazole Monoboronic Acid Fluorescent Sensors for the Selective Detection of alpha-Hydroxyl Carboxylic Acids and Monosaccharides[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,2009,131(47):17452-17463.
APA Zhang, Xin.,Chi, Lina.,Ji, Shaomin.,Wu, Yubo.,Song, Peng.,...&Zhao, Jianzhang.(2009).Rational Design of d-PeT Phenylethynylated-Carbazole Monoboronic Acid Fluorescent Sensors for the Selective Detection of alpha-Hydroxyl Carboxylic Acids and Monosaccharides.JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,131(47),17452-17463.
MLA Zhang, Xin,et al."Rational Design of d-PeT Phenylethynylated-Carbazole Monoboronic Acid Fluorescent Sensors for the Selective Detection of alpha-Hydroxyl Carboxylic Acids and Monosaccharides".JOURNAL OF THE AMERICAN CHEMICAL SOCIETY 131.47(2009):17452-17463.
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