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Selenium-containing core-expanded naphthalene diimides for high performance n-type organic semiconductors

Science China Chemistry 2020年第9期63卷 1182-1190页

作者： Wenjie Han Zhongli Wang Yunbin Hu Xiaodi Yang Congwu Ge Xike Gao Key Laboratory of Synthetic and Self-Assembly Chemistry for Organic Functional Molecules Centre for Excellence in Molecular SynthesisShanghai Institute of Organic ChemistryUniversity of Chinese Academy of SciencesChinese Academy of SciencesShanghai 200032China Experiment Center for Science and Technology Shanghai University of Traditional Chinese MedicineShanghai 201203China

The incorporation of heavy atoms into molecular backbone is an extremely straightforward strategy for fine-tuning the optoelectronic properties of organic ***,it is rarely studied in n-type small ***,by selenium substitution of NDI3 HU-DTYM2,two Se-decorated core-expanded naphthalene diimides(NDI)derivatives DTYM-NDI3 HUDSYM(1)and NDI3 HU-DSYM2(2)were *** comparison with the reference S-containing compound NDI3 HUDTYM2,the highest occupied molecular orbital(HOMO)and lowest unoccupied molecular orbital(LUMO)energy levels of 1 and 2 were fine-tuned with?HOMO of about 0.2 e V,?LUMO of 0.1 e V and the narrowed HOMO-LUMO *** surprisingly,the as-spun organic thin film transistors(OTFTs)based on 1 and 2 both showedμe,satvalues as high as1.0 cm2 V-1 s-1,which are 2-fold higher than that of NDI3 HU-DTYM2 with the same device structure and measurement *** addition,the single crystal OFET devices based on Se-containing compound NDI2 BO-DSYM2 showed a highμe,satvalue of 1.30 cm2 V-1 *** molecular packing of NDI2 BO-DSYM2 in single crystals(two-dimensional supramolecular structure formed by intermolecular Se···Se interactions)is quite different from that of a S-containing compound NDI-DTYM2(one dimensional supramolecular structure formed by intermolecularπ-πstacking).Therefore,the Se substitution can cause dramatic change about molecular stacking model,giving rise to high n-type OTFT *** results demonstrated an effective strategy of the heavy atom effect for designing novel organic semiconductors.

关键词： organic semiconductors selenium naphthalene diimides organic thin film transistors charge mobility

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Tuning the Charge Transport Property of naphthalene Diimide Derivatives by Changing the Substituted Position of Fluorine Atom on Molecular Backbone

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Chinese Journal of Chemistry 2014年第10期32卷 1057-1064页

作者： Xiao Zhang Zhongli Wang Shiyan Chen Zheng Zhao Wei Yuan Huaping Wang Xike Gao State Key Laboratory for Modification of Chemical Fibers and Polymer Materials Key Laboratory of High-Performance Fiber and ProductMinistry of EducationCollege of Materials Science and EngineeringDonghua University201620 ShanghaiChina Key Laboratory of Synthetic and Self-Assembly Chemistry for Organic Functional Molecules Shanghai Institute of Organic ChemistryChinese Academy of Sciences200032 ShanghaiChina

Three naphthalene diimides(2,3 and 4)fused with 2-(1,3-dithiol-2-ylidene)-2-fluorophenylacetonitrile moieties were designed and *** to the different substituted positions of fluorine atom on the phenyl group,the solution-processed thin films of 2 and 3 operated in air as n-channel transistors,while the films of 4 performed as ambipolar transistors,indicating that the variation of substituted position of fluorine atom on molecular backbone may tune the material’s charge transport behavior.

关键词： naphthalene diimides fluorine organic semiconductor organic field effect transistor

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naphthalene Diimide Templated Synthesis of Pillar[6]arenes

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Chinese Journal of Chemistry 2015年第3期33卷 339-342页

作者： Hua Ke Chen Jiao Yu-Heng Qian Mei-Jin Lin Jian-Zhong Chen College of Chemistry Fuzhou UniversityFuzhouFujian 350116China State Key Laboratory of Structural Chemistry Fujian Institute of Research on the Structure of MatterChinese Academy of SciencesFuzhouFujian 350002China

A facile method for the selective synthesis of pillar[6]arenes has been *** to a strong electron do-nor-acceptor interaction between the electron-deficient naphthalene diimide and a precursor for the pillararene,1,4-diisobutoxy-2,5-bis(methoxymethyl)benzene,naphthalene diimide has been demonstrated to act as a template for selective synthesis of pillar[6]arene in a modest yield(30%).

关键词： pillararenes naphthalene diimides templated synthesis donor-acceptor interactions

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