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Structural effect of fluorophore on phenylboronic acid fluorophore/cyclodextrin complex for selective glucose recognition

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Frontiers of Chemical Science and Engineering 2020年第1期14卷 53-60页

作者： Takeshi Hashimoto Mio Kumai Mariko Maeda Koji Miyoshi Yuji Tsuchido Shoji Fujiwara Takashi Hayashita Department of Materials and Life Sciences Faculty of Science and TechnologySophia UniversityTokyo102-8554Japan Department of Life Science and Medical Bioscience Graduate School of Advanced Science and EngineeringWaseda University(TWIns)Tokyo162-8480Japan Department of Current Legal Studies Faculty of LawMeiji Gakuin UniversityKanagawa244-8539Japan

Based on the design of the fluorescent site of a fluorescent probe,we have created a unique system that changes its twisting response to *** probes were synthesized,in which phenylboronic acid and two kinds of aromatic fluorescent site(pyrene or anthracene)were conjugated by an amide *** the fluorescence measurement of pyrene-type probe 1,dimer fluorescence was observed at high *** induced circular dichroism(ICD)experiments,a response was observed only in the presence of glucose and γ-cyclodextrin,and no response was seen with *** the other hand,in the fluorescence measurement of anthracene-type probe 2,dimer fluorescence was observed in the presence of both glucose and galactose,and the fluorescence was different from the case of *** the ICD spectra of these inclusion complexes were measured,an inversion of the Cotton effect,which indicates a change in the twisted structure,was observed in galactose and *** differences in response to monosaccharides may originate in the interaction between the fluorescent site and the cyclodextrin cavity.

关键词： sugar recognition phenylboronic acid cyclodextrin fluorescence response induced circular dichroism

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Mechanistic insights into the novel glucose-sensitive behavior of P(NIPAM-co-2-AAPBA)

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Science China Chemistry 2020年第3期63卷 377-385页

作者： Qingxian Wang Mian Fu Ying Guan Tony D.James Yongjun Zhang Key Laboratory of Functional Polymer Materials and State Key Laboratory of Medicinal Chemical Biology Institute of Polymer ChemistryCollege of ChemistryNankai UniversityTianjin 300071China Department of Chemistry University of BathClaverton DownBath BA27AYUK

A glucose-sensitive polymer,poly(N-isopropylacrylamide-co-2-acrylamidophenylboronic acid)(P(NIPAM-co-2-AAPBA)),was synthesized by reversible addition fragmentation chain transfer(RAFT)*** of glucose results in reduced solubility and hence increased turbidity,rather than the normal increase in solubility(decreased turbidity)observed for other PBA-based glucose-sensitive *** novel glucose-sensitive behavior is explained by a new mechanism,in which glucose acts as an additive and depresses the lower critical solution temperature(LCST)of the polymer,instead of increasing solubility by increasing the degree of ionization of the PBA *** and theoretic analysis for the influence of glucose on the thermal behavior of P(NIPAM-co-2-AAPBA)reveals that glucose depresses the LCST of P(NIPAM-co-2-AAPBA)copolymers in a two-stage manner,a fast decrease at low glucose concentrations followed by a slow decrease at high glucose *** low glucose concentrations,the binding of glucose with PBA groups on the polymer chain increases the number of glucose molecules proximal to the polymer which influences the thermal behavior of the polymer,causing a rapid decrease in ***,the transition occurs at a glucose concentration equal to the reciprocal of the binding constant between PBA and glucose,thus providing a novel method to determine the binding *** saccharides,including mannose,galactose and fructose,also depress the LCST of P(NIPAM-co-2-AAPBA)copolymer in the same way.

关键词： glucose-sensitive mechanism phenylboronic acid thermosensitive binding constant lower critical solution temperature polymers

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Carbonylative Coupling of 4,4’-Diiodobiphenyl Catalyzed by Pd(NHC) Complex

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Green and Sustainable Chemistry 2013年第1期3卷 15-18页

作者： Do-Hun Lee Jung-Tai Hahn Dai-Il Jung Department of Beautycare Youngdong University Youngdong South Korea Department of Chemistry Dong-A University Busan South Korea

To develop a luminescent material with high color purity, luminous efficiency, and stability, we synthesized diketone by carbonylative Suzuki coupling in the presence of Pd(NHC) complex as the catalyst. Carbonylative coupling of 4,4’-diiodobiphenyl and phenylboronic acid was investigated to study in detail the catalytic ability of the Pd(NHC) complex. Reactions were carried out using both CO and metal carbonyls. Bis-(1,3-dihydro-1,3-dimethyl-2H-imidazol- 2-ylidene) diiodo palladium was used as the catalytic complex. Reaction products biphenyl-4,4’-diylbis (phenyl- methanone) 3 and (4’-iodobiphenyl-4-yl)(phenyl) methanone 4 were obtained as a result of CO insertion into the palladium(II)-aryl bond. However, when pyridine-4-yl boronic acid was used in place of phenylboronic acid as the starting reagent, synthetic reaction yielding 3 and 4 were found not to occur.

关键词： Carbonylative Coupling Metal Carbonyl Pd(NHC) Complex 4 4’-Diiodobiphenyl phenylboronic Acid

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