A series of anthracene-based derivatives, namely, 9-（4-phenyl）anthracene（1）, 9-（4-phenylethynyl）- anthracene（2） and 9, 10-bis（phenylethynyl）anthracene（3）, was synthesized by the Suzuki/Sonogashira cross-co...A series of anthracene-based derivatives, namely, 9-（4-phenyl）anthracene（1）, 9-（4-phenylethynyl）- anthracene（2） and 9, 10-bis（phenylethynyl）anthracene（3）, was synthesized by the Suzuki/Sonogashira cross-coupling reactions in good yields. These compounds were fully characterized by X-ray crystallography, thermogravimetric analysis（TGA）, differential scanning calorimetry（DSC）, UV-Vis absorption and fiuorescence（FL） spectroscopy, as well as density functional theory（DFT） calculations. Single-crystal X-ray analysis revealed that the packing structures were influenced by the terminal substitutions. All the compounds exhibited high thermal stability（Td=221---484 ~C） and blue emission with a high quantum yield（~bf =0.20--0.75）. As the number of substituents increased, the decomposition temperatures（Td） of these compounds increased in the following order： 1〈2〈3. Experiments on the photophysical properties revealed that different substituents strongly affected the optical properties. In particular, compound lb with the electron-withdrawing group（--CHO） exhibited a larger Stokes shift（113 nm） than the other compounds. Investigation of the electrochemical properties of these compounds showed that the HOMO-LUMO energy gaps（Egap） decreased obviously as the degree of conjugation increased.展开更多
The development of sensors that recognize Lewis oligosaccharides can help the diagnosis and early detection of cancer. Herein, we reported the design and synthesis of a series of anthracene-based bisboronic acids （9a...The development of sensors that recognize Lewis oligosaccharides can help the diagnosis and early detection of cancer. Herein, we reported the design and synthesis of a series of anthracene-based bisboronic acids （9a-9e） with different N-substituents near the boronic acid unit. Among them, compound 9a could recognize sialyl Lewis X（sLex） with selectivity over other Lewis sugars, and could significantly stain sLeX-expressing HEPG2 cells with selectivity over the range of 0.1-10 μmol/L. Compound 9a possibly has two properly positioned boronic acids caused by the steric hindrance by the near N-benzyl substituent group, which empower its sLe^x selectivity and higher binding affinity.展开更多
Sensors capable of recognizing cell surface carbohydrates,such as sialyl Lewis X（sLe-x）,are invaluable research tools and for the diagnosis and early detection of many forms of cancer.In this paper,we report the des...Sensors capable of recognizing cell surface carbohydrates,such as sialyl Lewis X（sLe-x）,are invaluable research tools and for the diagnosis and early detection of many forms of cancer.In this paper,we report the design and synthesis of a series of bisboronic acids 6（a-f） as fluorescent sensors towards mono-/oligosaccharides.Among them,compounds 6d and 6e showed strong binding affinities with glucose and fructose,while compound 6c,in which two anthracene-based boronic acid units were linked by a hexamethylene spacer,was able to recognize sLe-x selectivity and stained HEPG2 cells at 1 μmoI/L.展开更多
基金Supported by the National Natural Science Foundation of Chflm（Nos.21602014, 61474144）, the Scientific Research Foundation for the Returned Overseas Chinese Scholars, State Education Ministry of China, the Fund Program for the Scientific Activities of Selected Returned Overseas Professionals of Beijing, China, the Scientific Research Common Program of Beijing Municipal Commission of Education, China, the Doctoral Scientific Research Foundation of Beijing Institute of Graphic Com- munication（BIGC）（No.KM201510015003） and the BIGC Project, China（Nos. 20190116002/043, 04190117001/019）.
文摘A series of anthracene-based derivatives, namely, 9-（4-phenyl）anthracene（1）, 9-（4-phenylethynyl）- anthracene（2） and 9, 10-bis（phenylethynyl）anthracene（3）, was synthesized by the Suzuki/Sonogashira cross-coupling reactions in good yields. These compounds were fully characterized by X-ray crystallography, thermogravimetric analysis（TGA）, differential scanning calorimetry（DSC）, UV-Vis absorption and fiuorescence（FL） spectroscopy, as well as density functional theory（DFT） calculations. Single-crystal X-ray analysis revealed that the packing structures were influenced by the terminal substitutions. All the compounds exhibited high thermal stability（Td=221---484 ~C） and blue emission with a high quantum yield（~bf =0.20--0.75）. As the number of substituents increased, the decomposition temperatures（Td） of these compounds increased in the following order： 1〈2〈3. Experiments on the photophysical properties revealed that different substituents strongly affected the optical properties. In particular, compound lb with the electron-withdrawing group（--CHO） exhibited a larger Stokes shift（113 nm） than the other compounds. Investigation of the electrochemical properties of these compounds showed that the HOMO-LUMO energy gaps（Egap） decreased obviously as the degree of conjugation increased.
基金Supported by the National Natural Science Foundation of China（No.21372060）, the Natural Science Fund for Distinguished Young Scholars of Hebei Province, China（No.B2015201005）, the Natural Science Foundation of Hebei Province, China （No.B2018201234） and the Foundation of Hebei Education Department, China （No.QB2017015）.
文摘The development of sensors that recognize Lewis oligosaccharides can help the diagnosis and early detection of cancer. Herein, we reported the design and synthesis of a series of anthracene-based bisboronic acids （9a-9e） with different N-substituents near the boronic acid unit. Among them, compound 9a could recognize sialyl Lewis X（sLex） with selectivity over other Lewis sugars, and could significantly stain sLeX-expressing HEPG2 cells with selectivity over the range of 0.1-10 μmol/L. Compound 9a possibly has two properly positioned boronic acids caused by the steric hindrance by the near N-benzyl substituent group, which empower its sLe^x selectivity and higher binding affinity.
基金supported by the National Natural Science Foundation of China(NSFC)(No.21372060)Hebei Province Natural Science Fund for Distinguished Young Scholars(No.B2015201005)
文摘Sensors capable of recognizing cell surface carbohydrates,such as sialyl Lewis X（sLe-x）,are invaluable research tools and for the diagnosis and early detection of many forms of cancer.In this paper,we report the design and synthesis of a series of bisboronic acids 6（a-f） as fluorescent sensors towards mono-/oligosaccharides.Among them,compounds 6d and 6e showed strong binding affinities with glucose and fructose,while compound 6c,in which two anthracene-based boronic acid units were linked by a hexamethylene spacer,was able to recognize sLe-x selectivity and stained HEPG2 cells at 1 μmoI/L.
