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phthalimide and Naphthalimide end-Capped Diketopyrrolopyrrole for Organic Photovoltaic Applications

Chinese Journal of Chemistry 2017年第9期35卷 1396-1404页

作者： Ming Chen Chenchen Du Xiaolei Ren Maoheng Yi Jinduo Yi Chufeng Chen Feng Liu Minjie Li Changqi Ma Hongyu Wang Department of Chemistry College of Science Shanghai University 99 Shangda Road Shanghai 200444 China Printable Electronics Research Center Suzhou Institute of Nano-Tech and Nano-Bionics Chinese Academy of Sciences 398 Ruo Shui Road SEID SIP Suzhou Jiangsu 215123 China No. 2 High School Affiliated to East China Normal University Zizhu 350 Zifeng Road Minhang District Shanghai 200241 China Department of Physics and Astronomy Shanghai Jiao Tong University 800 Dongchuan Road Shanghai 200240 China

Two small molecules named PI-DPP and NI-DPP with a DPP core as the central strong acceptor unit and phthalimide/naphthalimide as the terminal weak acceptor were designed and synthesized. The effects of terminal phthalimide/naphthalimide units on the thermal behavior, optical and electrochemical properties, as well as the photovoltaic performance of these two materials were systematically studied. Cyclic voltammetry revealed that the lowest unoccupied molecular orbitals （LUMO）（- -3.6 eV） of both molecules were intermediate to common electron donor （P3HT） and acceptor （PCBM）. This indicated that PI-DPP and NI-DPP may uniquely serve as electron donor when blended with PCBM, and as electron acceptor when blended with P3HT, where sufficient driving forces between DPPs and PCBM, as well as between P3HT and DPPs should be created for exciton dissociation. Using as electron donor materials, PI-DPP and NI-DPP devices exhibited low power conversion efficiencies （PCEs） of 0.90% and 0.76% by blending with PCBM, respectively. And a preliminary evaluation of the potential of the NI-DPP as electron acceptor material was carried out using P3HT as a donor material, and P3HT：NI-DPP device showed a PCE of 0.6%, with an open circuit voltage （Voc） of 0.7 V, a short circuit current density （Jsc） of 1.91 mA·cm^-2, and a fill factor （FF） of 45%.

关键词： diketopyrrolopyrrole phthalimide naphthalimide organic solar cells non-fullerene acceptor

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Synthesis and cytotoxic activity of heterocycle-substituted phthalimide derivatives

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Chinese Chemical Letters 2010年第8期21卷 902-904页

作者： Ya Jun Yang Ya Nan Yang Jian Shuang Jiang Zi Ming Feng Hong Yan Liu Xian Dao Pan Pei Cheng Zhang Key Laboratory of Bioactive Substances and Resources Utilization of Chinese Herbal Medicine(Ministry of Education) Institute of Materia MedicaPeking Union Medical College and Chinese Academy of Medical SciencesBeijing 100050China Beijing Union Pharmaceutical Factory Beijing 102600China

A series of heterocycle-substituted phthalimide derivatives were *** diverse derivatives with heterocyclic rings,including furan,imidazo[1,2-a]pyridine,1,3,4-thiadiazine,imidazo[2,1-b][1,3,4]thiadiazine,pyrazole,1,2,4-triazolo[3,4- b][1,3,4]thiadiazine,thiazole and thiazoline,were obtained by the reactions ofα-bromoketone intermediate with various nucleophiles containing oxygen,nitrogen and sulfur *** cytotoxic activity was also evaluated against five human cancer cell lines in vitro.

关键词： phthalimide Heterocycle α-Bromoketone Cytotoxic activity

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An Unusual Reductive Ring-opening Reaction of phthalimide with Sodium Hydride in DMF

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Chinese Chemical Letters 2004年第7期15卷 777-778页

作者： XiangBaoMENG HuiLI QingLI ZhongJunLI DepartmentofChemicalBiology SchoolofPharmaceuticalSciencesPekingUniversityBeijing100083

An unusual reductive ring-opening reaction of phthalimide with sodium hydride in anhydrous DMF was observed for the first time. The presumed mechanism was described in detail.

关键词： phthalimide benzylation reduction ring-opening.

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Synthesis, Spectral Characterization and Ligation of <i>N</i>-[2-(Phenylseleno)ethyl]phthalimide

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Journal of Crystallization Process and Technology 2013年第1期3卷 31-34页

作者： Rupali Rastogi Sanjay Kumar Srivastava Shikha Asolia Raymond J. Butcher Department of Chemistry Howard University Washington DC USA School of Studies in Chemistry Jiwaji University Gwalior India

PhSe-Na+ generated in situ by reduction of PhSeSePh, with sodium borohydride on reaction with N-(2-bromoethyl) phthalimide in N2 atmosphere results in the formation of N-[2-(phenylseleno)ethyl]phthalimide (L1). The title compound has been characterized by elemental analysis, FT-IR, 1H and 13C NMR techniques. The crystal structure of L1 has been solved by direct methods and refined by full-matrix least squares. The ligand L1 crystallize in the monoclinic space group. Selenium forms two Se-C linkages, one is due to Se-Calkyl and the other one to Se-Caryl. Further, the ligation reaction of L1 with complex 1 is also explored whose identities are characterized by spectroscopic techniques.

关键词： phthalimide Selenium Monoclinic Phenylseleno Sodium Borohydride

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Synthesis and reversal effect of a novel N-substituted phthalimidesugar on doxorubicin resistant of human breast cancer cells

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Journal of Chinese Pharmaceutical Sciences 2008年第4期17卷 319-323页

作者：易文渊李敏杨亚平吕卓远徐波韩冬李中军崔景荣北京大学天然药物及仿生药物国家重点实验室北京100191 北京大学药学院化学生物学系北京100191

Thalidomide （α-N-phthalimido-glutarimide, TLD） is a kind of anti-angiogenic and anti-inflammatory drug, and showed effects in the treatment of several disease entities. In this study, the biological effects of a novel N-sugar substituted phthalimide （STA-35） on the regulation of multidrug resistance （MDR） to doxorubicin （ADR） were investigated. The proliferation of cancer cells was detected by a SRB assay. The activity of P-glycoprotein （P-gp） was determined by a Flow cytometry. The expression of P-gp was measured by western blotting. The results showed that STA-35 inhibited the proliferation of human breast cancer cell line MCF-7 and its ADR resistant cell line MCF-7/ADR, and the relative resistance was only 1.19. Meanwhile, STA-35 could sensitize the cytotoxicity of ADR in MCF-7/ADR cells. In addition, we found that STA-35 reduced the activity of P-gp by suppressing the P-gp expression, which was indicated by the increase in the accumulation of rhodamine 123 in MCF-7/ADR cells. These results suggested a promising application of STA-35 as the MDR reversing agent. The underlying mechanism of the effects might be attributed to the inhibition of P-gp.

关键词： Multidrug resistance Thalidomide phthalimide P-glycoprotein

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A Versatile Approach for the Asymmetric Synthesis of 3-Alkyl-isoindolin-1-ones

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Chinese Journal of Chemistry 2002年第11期20卷 1149-1153,1124页

作者：陈明德贺明珠黄利强阮源萍黄培强 Department of Chemistry Xiamen University Xiamen Fujian 361005 China

A flexible approach to (R)-3-alkyl-isoindolin-1-ones and (R)-3-aryl-isoindolin-l-ones via a diastereoselective reductive-alkylation is described. Present method is versatile in scope, allowing the easy introduction of various C-3 substituents by Grignard addition to phthalimide derived from (R)-phenylglycinol. 3-Alkyl-3-hydroxy-isoindolin-1-ones can also be obtained in the first step of the present method.

关键词： isoindolin-1-one asymmetric synthesis phenylglycinol reductive allkylation phthalimide

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Synthesis of Novel Non-Nucleoside HIV-1 Reverse Transcriptase Inhibitors-1-(3-Phthalimido-2-oxobutyl)-4-Substituted-phenylpiperazines

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Chinese Chemical Letters 2000年第7期11卷 571-572页

作者： Xin CHEN Lin WANG Zhi Zhong ZHAO Xing Quan ZHANG Xiang Hong CHEN Hong Shan CHEN(Institute of Materia Medica, Chinese Academy of Medical Sciences & Peking Union Medical College, Beijing 100050 Institute of Medicinal Biotechnology, Chinese Academy of M Institute of Materia Medica Chinese Academy of Medical Sciences Peking Union Medical College Beijing 100050 China Institute of Medicinal Biotechnology Chinese Academy of Medical Sciences Peking Union Medical College Beijing 100050 China

We have designed and synthesized a series of new phthalimidopiperazines, biological activity test show that the target compounds(Ic, Ie, ii) can inhibit HIV-I RT with IC50 20.0, 43.8, and 63.7 mu M, respectively.

关键词： piperazine phthalimide HIV1-RT inhibitor

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Organic solar cells fabricated from PhI-based polymers and DPP-based small molecules

Organic solar cells fabricated from PhI-based polymers and D...

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第十三届全国光化学学术讨论会

作者： Jianhua Huang Hui Jia Chuanlang Zhan Jiannian Yao Institute of Chemistry Chinese Academy of Sciences

＜正＞Organic solar cells have been a rather active area in organic electronics due to their potential applications to afford low-cost and green energy. In order to obtain high efficiency materials, we choose phthalimide （PhI） and diketopyrrolopyrrole （DPP）, respectively, as basic units to construct a series of copolymers and solution-processed small molecules. The effects of intermolecular and intramolecular interactions on photovoltaic performances were investigated.

关键词： organic solar cells conjugated copolymers solution-processed molecules diketopyrrolopyrrole phthalimide

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