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SyNTHESIS AND PHOTOLUMINESCENCE OF AN ANTHRACENE-CONTAINING HyPERBRANCHED POLy(ARyLENEETHyNyLENE)

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Chinese Journal of Polymer Science 2005年第6期23卷 665-669页

作者： yong-qiang Dong Zhen Li jacky w. y. lam yu-ping Dong Xin-de Feng Ben-zhong Tang Department of Polymer Science and Engineering College of Chemistry and Molecular Engineering Peking University Beijing 100871 China Department of Chemistry Center for Display Research The Hong Kong University of Science ＆ Technology Clear Water Bay Kowloon Hong Kong China

A hyperbranched poly（aryleneethynylene） containing anthracene chromophore was synthesized by palladiumcatalyzed cross-coupling reaction of 2,4,6-triiodophenyl 9-anthracenylcarboxylate with 9,9-bis[4-（2-propynyloxy）phenyl]- 9H-fluorene. The structure and properties of the polymer are characterized and evaluated by NMR, IR, UV, PL and TGA analyses. The polymer is soluble in common organic solvents, possesses high thermal stability （Td 〉 330℃）, and emits a strong blue light of 465 nm in both solution and solid states.

关键词： Hyperbranched polymer Cross-coupling Blue light emission

SyNTHESIS,HELICITy,AND BIOLOGICAL PROPERTIES OF MONOSACCHARIDE-CONTAININGPOLy(PHENyLACETyLENE)S

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Chinese Journal of Polymer Science 2007年第2期25卷 119-122页

作者： jacky w. y. lam Kevin K. L. Cheuk Bing-shi Li yong Xie Ben-zhong Tang Department of Chemistry The Hong Kong University of Science ＆ Technology Clear Water Bay Kowloon Hong Kong China Department of Biology The Hong Kong University of Science ＆ Technology Clear Water Bay Kowloon Hong Kong China Department of Polymer Science ＆ Engineering Zhejiang University Hangzhou 310027 China

Poly（phenylacetylene）s beating monosaccharide pendant groups are synthesized in high yields by [Rh（nbd）Cl]2 catalyst. The polymers have high molecular weights and give satisfactory spectroscopic data corresponding to their molecular structures. They are thermally quite stable （≥ 300℃） and show strong circular dichroism signals in the visible spectral region owing to the helicity of the polyene backbone. The monosaccharide-containing polyacetylenes are cytophilic and can stimulate the growth of living cells.

关键词： Biocompatibility Biomimetic Helicity Monosaccharides Polyacetylenes Sugars.

Crystalline Behavior and Structure of a Liquid Crystal Com- pound, 5-{[4＇-（（（Pentyl）oxy）-4-biphenylyl）carbonyl]oxy}- 1 -pentyne

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Chinese Journal of Chemistry 2011年第4期29卷 631-638页

作者：刘雷静李杲周恩乐 lam,jacky wing yip 唐本忠 State Key Laboratory of Supramolecular Structure and Materials Jilin University Changchun Jilin 130012 China State Key Laboratory of Polymer Physics and Chemistry Changchun Institute of Applied Chemistry Chinese Academy of Sciences Graduate School of Chinese Academy of Sciences Changchun Jilin 130022 China Department of Chemistry Hong Kong University of Science & Technology Clear Water Bay Kowloon Hong Kong China

Single crystals of two liquid crystal compounds, 5-{[4＇-（（（pentyl）oxy）-4-biphenylyl）carbonyl]oxy}-1-pentyne （A3EO5） and 5-{[（4＇-nonyloxy-4-biphenylyl）carbonyl]oxy}-1-pentyne （A3EO9）, have been prepared by solution growth technique. The morphologies and structures of A3EO5 and A3EO9 crystals were investigated by wide angle X-ray diffraction （wXRD）, atom force microscope （AFM） and transmission electron microscope （TEM）. In contrast to the same series of compounds which have a longer alkyl tail, 5-{[（4＇-heptoxy-4-biphenylyl）carbonyl]oxy}-1-pentyne （A3EO7）, 5-{[（4＇-heptoxy-4-biphenylyl）oxy]carbonyl}-1-pentyne （A3E＇O7） and A3EO9, A3EO5 shows strikingly different crystalline behavior. The former three compounds have only one crystal form, whereas A3EO5 exhibits polymorphism. Specifically, A3EO5 crystals grown from toluene solution show two crys- tal forms. The first one is crystal I which adopts a monoclinic P112/m space group with unit cell parameters of a= 5.79A, b=8.34A, c=43.92/k, y=96°, and the other one is crystal II which adopts a monoclinic P112 space group with unit cell parameters of a=5.55A, b=7.38A, c=31.75 ]k, y=94°. when using dioxane as the solvent to grow A3EO5 crystal, we can selectively obtain crystal Ⅰ. A3EO5 melt-grown crystals also have two crystal forms which derive from crystal I and crystal Ⅱ, respectively. The different crystalline behavior of the compounds should correlate with their different electron dipole moment resulting from the different length of alkyl tail.

关键词： crystal growth crystal morphology crystal structure electron diffraction single crystal

Synthesis of an AIE-active fluorogen and its application in cell imaging

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Science China Chemistry 2009年第1期52卷 15-19页

作者： lam jacky wing yip FAISAL Mahtab NG Ka Ming LUO Kathy Qian Department of Chemistry The Hong Kong University of Science & Technology (HKUST) Clear Water Bay Department of Chemical and Biomolecular Engineering HKUST Clear Water Bay Bioengineering Graduate Program HKUST Clear Water Bay

A fluorogen named 1-decyl-1-methyl-2,5-bis{4-[(N,N-diethylamino)methyl]phenyl}-3,4-diphenylsilole (3) was synthesized. It emitted weakly as isolated molecule but strongly as supramolecular aggregate, showing a characteristic behavior of aggregation-induced emission (AIE). The molecules of 3 formed highly emissive nanoparticles in aqueous media, which quickly and selectively marked cytoplasm of HeLa cells and posed no toxicity to the living cells. The fluorogen is thus a promising candidate mate-rial for cell imaging as a sensitive, selective and cytocompatible biosensor.

关键词： aggregation-induced emission biosensor cell imaging

1-((12-Bromododecyl)oxy)-4-((4-(4-pentylcyclohexyl)phenyl)ethynyl) benzene: Liquid crystal with aggregation-induced emission characteristics

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Science China Chemistry 2013年第9期56卷 1191-1196页

作者： CHEN yaFei LIN JieSheng yUAN wangZhang yU ZhenQiang lam jacky wingyip TANG Ben Zhong Shenzhen Key Laboratory of Functional Polymers School of Chemistry and Chemical EngineeringShenzhen University National Institutes for Food and Drug Control School of Chemistry and Chemical engineering Shanghai Jiao Tong University Department of Chemistry The Hong Kong University of Science & Technology

The luminescent liquid crystals (LLCs) are expected to solve the conflicts between the aggregation caused quenching and the requirement of aggregation or self-organization for LCs. Herein, we developed a new strategy of applying aggregation-induced emission (AIE) phenomenon to the molecular design of LCs towards LLCs. In this report, a calamitic liquid crystal based on tolane with AIE characteristics was successfully synthesized and the chemical structure was characterized by 1H, 13C NMR, and matrix-assisted laser desorption/ionization time-of-flight (MALDI-TOF) high-resolution mass spectra. The fluorescence behavior was studied by fluorescence spectroscopy and the liquid crystal phase behaviors were investigated by differential scanning calorimetry (DSC), polarized optical microscopy (POM). The crystal structure was obtained by X-ray diffraction crystallography with P1 space group. Results demonstrated that the sample was AIE active and the LC phases sequence during cooling was nematic, smectic C and smectic B phase.

关键词： aggregation-induced emission tolane liquid crystal phase behavior

HyPERBRANCHED CONJUGATIVE MACROMOLECULES CONSTRUCTED FROM TRIPLE-BOND BUILDING BLOCKS

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Chinese Journal of Polymer Science 2005年第6期23卷 567-591页

作者： Matthias HaeuBler Hong-chen Dong jacky wing yip lam Rong-hua Zheng An-jun Qin Ben-zhong Tang Department of Chemistry The Hong Kong University of Science ＆ Technology Clear Water Bay Kowloon Hong Kong China Department of Polymer Science and Engineering Zhejiang University Hangzhou 310027 China

Polycyclotrimerization and polycoupling of acetylenic monomers respectively furnish hyperbranched polyarylenes and polyynes with high molecular weights （up to 1 × 10^6） in high yields （up to 99.9%）. The polymers possess low intrinsic viscosities and high thermal stabilities, losing little of their weights when heated to 〉 400℃. Upon pyrolysis at 〉 800℃, the polymers graphitize with high char yields （up to 86%）. Hyperbranched polyarylenes efficiently emit deep-blue to blue-green lights with fluorescence quantum yields up to 98% and strongly attenuate intense laser pulses with optical power-limiting performances superior to that of C60, a well-known optical limiter. Poly（alkenephenylenes）, poly（aroylarylenes） and polyynes are readily cross-linkable by UV irradiation, serving as excellent photoresist materials for the generation of patterns with nanometer resolution. Thin films of hyperbranched polyynes exhibit very high refractive indexes （n up to 1.86）. The internal and terminal acetylene moieties of the polyynes readily form complexes with cobalt carbonyls, which can be transformed into soft ferromagnetic ceramics with high magnetic susceptibilities （Ms up to ca. 118 emu/g） and near-zero magnetic losses.

关键词： Hyperbranched polymers Alkyne polycyclotrimerization Alkyne polycoupling Polyarylenes Polyynes Optical materials Photoresists Soft ferromagnetic ceramics

具有不同长度间隔基的含联苯基团的侧链液晶聚炔的荧光行为(英文)

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物理化学学报 2010年第8期26卷 2281-2285页

作者：余振强张昕李子臣陈尔强 lam jacky w. y. 唐本忠北京大学化学与分子工程学院高分子科学与工程系高分子化学与物理教育部重点实验室北京分子科学国家实验室北京100871 深圳大学化学与化工学院深圳市功能高分子重点实验室广东深圳518060 香港科技大学化学系香港九龙

对一系列具有不同长度间隔基的含联苯基团的侧链液晶聚炔的稳态荧光和荧光衰减行为进行了研究.为便于比较,选取其中一个单体作为模型化合物.稳态荧光光谱结果表明,聚合物和单体均显示一个荧光发射,该荧光发射来源于聚合物侧链的联苯基团... 详细信息

对一系列具有不同长度间隔基的含联苯基团的侧链液晶聚炔的稳态荧光和荧光衰减行为进行了研究.为便于比较,选取其中一个单体作为模型化合物.稳态荧光光谱结果表明,聚合物和单体均显示一个荧光发射,该荧光发射来源于聚合物侧链的联苯基团.随着间隔基长度的减小,聚合物的荧光强度降低.荧光衰减结果表明单体的荧光衰减可以拟合为一个单指数衰减,而聚合物的荧光衰减拟合为三指数衰减.这种三指数衰减可能由溶液局部高浓度引起的猝灭和侧链联苯基团的旋转受阻所引起.溶剂效应表明,溶剂与联苯基团之间的相互作用随溶剂极性增加而增大.

关键词：稳态荧光单取代聚炔联苯荧光寿命溶剂效应

A facile design for multifunctional AIEgen based on tetraaniline derivatives

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Science China Chemistry 2019年第6期62卷 732-738页

作者： Beibei Liu wei He Hao Lu Kun wang Mingming Huang Ryan Tsz Kin Kwok jacky wing yip lam Longcheng Gao Jiping yang Benzhong Tang Key laboratory of Aerospace Advanced Materials and Performance Ministry of Education School of Materials Science and EngineeringBeihang University Department of Chemistry HKUST Jockey Club Institute for Advanced Study Institute of Molecular Functional Materials Division of Biomedical Engineering State Key Laboratory of Molecular Neuroscience Division of Life Science The Hong Kong University of Science and Technology Laboratory of Bio-Inspired Smart Interfacial Science and Technology of Ministry of Education Key Laboratory of Beijing Energy School of Chemistry and Environment Beihang University

Aniline oligomers have been widely used in many fields due to their excellent physicochemical properties. Owing to strong intermolecular interactions, their emission is always weakened or quenched when they are in high concentration or aggregated state, which greatly limits their fluorescent applications. Inspired by the concept of aggregation-induced emission(AIE), herein we introduced large steric groups onto the aniline oligomer to prevent the formation of packing structure. In particular, diphenyl vinyl group was bonded with oligomeric tetraaniline by a facile synthetic procedure with high yield. The obtained aniline oligomer derivative exhibited typical AIE features, which was also confirmed by density functional theoretical calculation. More importantly, this AIE oligomer was able to detect Fe^(3+) ions selectively and quantitatively. The fluorescence intensity decreased linearly along with the increment of Fe^(3+) concentration. Moreover, we demonstrated that this AIE oligomer could stain live bacteria, such as E. coli and S. aureus efficiently. All these results suggest that such a readily accessible and multifunctional tetraaniline derivative provides a new platform for the construction of fluorescent materials.

关键词： tetraaniline aggregation-induced emission Fe3+ ion detection bacteria imaging

具有聚集诱导发光效应的聚炔材料的合成及光学性能研究

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化学学报 2016年第11期74卷 877-884页

作者：韩婷詹嘉慧林荣业唐本忠香港科技大学化学系国家人体组织功能重建工程技术研究中心香港分中心香港科技大学深圳研究院深圳518057

合成了三种含有四苯基乙烯结构的双炔烃．这些双炔烃单体通过在CuCl催化下在邻二氯苯中进行的均聚反应可以高产率地生成线型聚炔．所得聚合物均可很好地溶解于常见有机溶剂中，并具有很高的热稳定性．这类聚炔材料在溶液态时几乎不发光... 详细信息

合成了三种含有四苯基乙烯结构的双炔烃．这些双炔烃单体通过在CuCl催化下在邻二氯苯中进行的均聚反应可以高产率地生成线型聚炔．所得聚合物均可很好地溶解于常见有机溶剂中，并具有很高的热稳定性．这类聚炔材料在溶液态时几乎不发光，但在聚集态或者固态下可高度发光，表现出典型的聚集诱导发光性质．同时，这些聚合物具有高透光性，可以允许整个可见光区的光透过．其薄膜在4001700nm宽波长范围内表现出高折射率（n=1．7787-1．6543）和低色差（D＇=0．0003）．紫外光照射可诱使聚合物薄膜发生交联过程，从而调控其折射率数值，并可生成高分辨率的荧光图案．

关键词：线型聚炔聚集诱导发光四苯基乙烯折射率