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Synthesis of a novel perylene diimide derivative and its charge transfer interaction with C_(60)

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Science China Chemistry 2008年第2期51卷 152-157页

作者： LIU Bo1,2, SHI MinMin1,2, YANG LiGong1,2, CHEN HongZheng1,2 & WANG Mang1,2 1 State Key Lab of Silicon Materials, Department of Polymer Science and Engineering, Zhejiang University, Hangzhou 310027, China 2 Key Laboratory of Macromolecule Synthesis and Functionalization of Ministry of Education, Zhejiang University, Hangzhou 310027, China State Key Lab of Silicon Materials Department of Polymer Science and Engineering Zhejiang University Hangzhou China Key Laboratory of Macromolecule Synthesis and Functionalization of Ministry of Education Zhejiang University Hangzhou China

A novel organic electron acceptor, N,N′-dipyrimidinyl-3,4,9,10-perylene-tetracarboxylic diimide (DMP), was designed and synthesized. The molecular structure was characterized by FTIR spectrum and elemental analysis. By cyclic voltammetry measurements, DMP was found to possess a lower LUMO energy level than N,N′-diphenyl-3,4,9,10-perylene-tetracarboxylic diimide due to the stronger electron-withdrawing pyrimidinyl group than the phenyl group. Fluorescence quenching is observed in a dual-layer film consisting of a DMP layer and a C60 layer and was attributed to the charge transfer at the interface due to the energy level offset between DMP and C60.

关键词： perylene diimide LUMO charge transfer fluorescence quenching

Mn(Ⅲ)-mediated radical cascade reaction of boronic acids with isocyanides:Synthesis of diimide derivatives

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Chinese Chemical Letters 2019年第2期30卷 379-382页

作者： Fei Wang Tian-Qi Wei Pei Xu Shun-Yi Wang Shun-Jun Ji Key Laboratory of Organic Synthesis of Jiangsu Province College of ChemistryChemical Engineering and Materials Science ξ Collaborative Innovation Center of Suzhou Nano Science and Technology Soochow University

A manganese (Ⅲ)-promoted oxidative radical cascade reaction of easily accessible arylboronic acids with isocyanides to construct diimide derivatives was studied. This protocol provides a new way to synthesis of acety... 详细信息

关键词： Mn(OAc)3 Isocyanide Arylboronic acid diimide derivatives Radical cascade

A new perylene diimide-based colorimetric and fluorescent sensor for selective detection of Cu^(2+) cation

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Science China Chemistry 2009年第4期52卷 518-522页

作者： YAN LiWei,YANG Li,LAN JingBo & YOU JingSong Key Laboratory of Green Chemistry and Technology of Ministry of Education,College of Chemistry,and State Key Laboratory of Biotherapy,West China Hospital,West China Medical School,Sichuan University,Chengdu 610064,China Key Laboratory of Green Chemistry and Technology of Ministry of Education College of Chemistry and State Key Laboratory of Biotherapy West China Hospital West China Medical School Sichuan University Chengdu China

A new perylene diimide (PDI) ligand (1) functionalized with a dipicolylethylenediamine (DPEN) moiety was synthesized and first used as a colorimetric and fluorometric dual-channel sensor to specifically detect the presence of Cu2+ over a wide range of other cations. The solution of 1 (10 μmol/L) upon ad-dition of Cu2+ displayed distinguishing pink color compared with other cations including K+,Ni2+,Ca2+,Mn2+,Na+,Sr2+,Zn2+,Co2+,Cd2+,Mg2+,Cr3+,Ag+,and Ba2+,indicating the sensitivity and selectivity of 1 to Cu2+. Thus,the advantage of this assay is that naked-eye detection of Cu2+ becomes possible. More-over,among these metal ions investigated,only Cu2+ quenched more than half fluorescent intensity of 1. The ESI-TOF spectrum of a mixture of 1 and CuCl2 in combination of the fluorescence titration spectra of 1 (10 μmol/L) upon addition of various amounts of Cu2+ revealed the formation of a 2︰1 metal-ligand complex through the metal coordination interaction.

关键词： perylene diimide (PDI) colorimetric fluorescent sensor copper ion

Synthesis and Evaluation of Novel 1,4,5,8-Naphthalenetetracarbox diimide Derivatives

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Synthesis and Evaluation of Novel 1,4,5,8-Naphthalenetetraca...

A twisted monomeric perylenediimide electron acceptor for efficient organic solar cells

河南省化学会2016年学术年会

作者： Li-Ping Chang Cong-Cong Chang Yuan Chang Yu-Xia Wang Chao-Jie Wang Key Laboratory of Natural Medicine and Immuno-Engineering Henan University College of Chemistry and Chemical Engineering Henan University

1,4,5,8-naphthalentetracarboxylic diimide derivatives have got general concern as a fluorescent dye and DNA intercalators and which showed the ability to intercalate into steps containing at least one G:C base pair. At the same time naphthalenediimide scaffold is present in a wide number of anticancer agents and which were more cytotoxic than the corresponding naphthalimide derivatives as anticancer agents. Now several anticancer agents recently published in literature are characterized by Naphtalene diimide scaffold. Nitrogen organic compounds have extensive biological activities and are widely used in pharmaceutical synthesis. So we functionalized 1,4,5,8-Naphthalenete-tracarboxylic dianhydride with two symmetrical nitrogen basic side chains to the target compounds. Four naphthaldiimide derivatives were designed and synthesized. The structures of all the target compounds were confirmed by H NMR, ESI-MS and elemental analysis. Their antitumor activities were evaluated against MDA-MB-231, MCF-7, HCT-116,HT-29, Hep G2, SMMC-7721 and K562 cancer cell lines in vitro. The results showed that the1,4,5,8-naphthalentetracarboxylic diimide derivatives displayed different inhibitive behaviors against tested tumor cells. All of the conjugates exhibited a degree of anti-tumor activities in all the tested tumor cells and have lower IC50 values against all the cell lines than the positive control amonafide.

关键词： synthesis anticancer diimide

来源： cnki会议评论

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Science China Materials 2016年第6期59卷 427-434页

作者：蔡芸皓郭谢友孙晓波魏东辉于明明霍利军孙艳明 Heeger Beijing Research and Development Center School of Chemistry and EnvironmentBeihang UniversityBeijing 100191China The College of Chemistry and Molecular Engineering Zhengzhou UniversityZhengzhou 450001China

Perylenediimide(PDI)-based materials exhibit great potential as non-fullerene acceptors in bulk-heterojunction(BHJ) organic solar cells(OSCs). Recent investigations have revealed that PDI molecules with a twisted structure could disrupt aggregation of perylene unit. Here, we present a PDI monomer via bay-substitutions with four fused naphthalene units by three-step reactions, named TN-PDI. The introduction of four fused naphthalene rings into the bay positions of PDI unit leads to a strong steric hindrance with a twist angle of 33° between the two PDI subplanes. Blended with a wide-band gap polymer donor(PDBT-T1), the TN-PDI based non-fullerene solar cells show power conversion efficiency(PCE) of 3.0%. Our results indicate that the bay-substitutions with fused aromatic substitutions could be an efficient approach to develop monomeric PDI acceptors.

关键词： organic solar cells non-fullerene electron acceptors perylene diimide monomer

Naphthalene-containing polyimides:Synthesis, characterization and photovoltaic properties of novel donor-acceptor dyes used in solar cell

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中国有色金属学会会刊：英文版 2009年第S3期19卷 587-593页

作者：牛海军穆景山张密林罗俊罗培辉白续铎王文 College of Materials Science and Chemical Engineering Harbin Engineering University Key Laboratory of Functional Inorganic Material Chemistry Ministry of EducationHeilong jiang University Key Laboratory of Functional Inorganic Material Chemistry Ministry of EducationHeilongjiang University Key Laboratory of Functional Inorganic Material Chemistry Ministryof EducationHeilongjiang University School of Materials Science and Engineering Harbin Institute of Technology

Novel linear and star branched triphenylamine-containing aromatic imides were designed and synthesized by the condensation between amine-substituted triphenylamine and naphthalene-1, 4, 5, 8-tetra-carboxylic dianhydride in order to investigate the influence of topological structure on the photophysical performance. The polyimides were characterized by elementary analysis and FTIR measurements. Thermogravimetric analysis (TGA) shows that the onset temperatures of decomposition (Td) for 5% mass loss range from 371 to 445 ℃. UV-Vis spectrum, quantum chemical calculation and cyclic voltammetry (CV) were used to obtain the dependence of energy levels on the function of structures. The introduction of triphenylamine group changes the energy level of the entire dye system. The dye-sensitized solar cells (DSSCs) prepared by using the dyes have a strong photoelectric current response in visible light region of 400-600 nm.

关键词： naphthalene diimide triphenylamine sensitized solar cell electrochemical properties

Increasing the Solubility of a Hydrophobic Molecule with Thymine-like Face by DNA via Supramolecular Interaction

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Chemical Research in Chinese Universities 2020年第2期36卷 281-284页

作者： SHI Peijun ZHANG Zhe LIU Mingchun SUN Teng HE Xiaoyan MAO Chengde FANG Liang ZUO Hua National Demonstration Center for Experimental Pharmacy Education(Southwest Universityj College of Pharmaceutical SciencesSouthwest UniversityChongqing 400715P.R.China Department of Oncology the Ninth People’s Hospital of ChongqingChongqing 400700P.R.China Department of Chemistry Purdue UniversityWest LafayetteIN47907USA

Poor water-solubility of hydrophobic drugs greatly hampers drug design and creats delivery *** traditional way to improve the solubility is to add hydrotropes or excipients to supress ***,a novel mechanisim has been proposed based on supramolecular interactions and demonstrated with a small molecule,pvromellitic diimide(PD).This compound contains thymine-like ‘face’ and can interact with adenines through Wat-son-Crick and Hoogsteen *** the high water solubility of poly adenines[poly(A)],it is expectec that poly(A)will greatly increase the PD ***,such an increased solubility was confirmed by ultraviolet-visible spectroscopy(UV-Vis)and polyacrylamide gel electrophoresis(PAGE)*** believe that this strategy could be used to improve the solubility of other similar hydrophobic molecules.

关键词： Polyadenine[poly(A)] Pyromellitic diimide Hydrogen bond force Increased solubility