Synthetic Studies on Organic Electric Conductors Containing Heteroatoms

含杂原子有机导电体的合成研究

• 批准号: 05453058
• 负责人: OGURA Fumio
• 金额: $ 4.74万
• 依托单位: HIROSHIMA UNIVERSITY
• 依托单位国家: 日本
• 项目类别: Grant-in-Aid for General Scientific Research (B)
• 财政年份: 1993
• 资助国家: 日本
• 起止时间: 1993 至 1994
• 项目状态: 已结题
• 来源: https://kaken.nii.ac.jp/en/grant/KAKENHI-PROJECT-05453058/
• 关键词: organic electric conductor; organic electron donor; organic electron acceptor; organic charge-transfer complex; heteroarene; dumbbell type TTF donor; hetero-TCNQ; anthracene-TCNQ

Novel heteroarenes, naphtho [1,8-bc : 5,4-b'c'] -and Naphtho[1,8-bc : 4,5-b'c'] -dithiophenes (anti-and syn-NDT), isoelectronic with pyrene, were synthesized as new electron donors. Electron donating CT complexes with iodine and DDQ.2,3,6,7-Tetrathiabenzo [1,3-cd : 4,6-c'd'] dipentalene (TBD) was synthesized as a novel electron donor isoelectronic with perylene.TBD has about the same donor ability and formed a relativaly high conductive iodine complex. Various substitution derivatives of 2- (thiopyran-4'-ylidene) -1,3-dithiole and selenium analogues were syuthesized as novel electron donors.Systematic studies on them afforded many highly conductive CT complexes. Pyranylidenemethy1-and thiopyranylidenemethy1-substituted furans, thiophenes, and N-methy1pyrroles were synthesized as precursors of organic metals. Both of the N-methy1pyrroles afforded highly conductive CT complexes with TCNQ.High conductivities of radical cation salts of anthra [1,9-cd : 4,10-c'd'] bis [1,2] dichacogenoles w … More ere studied with their solid structures.2,2'-Bi-and 2,2'5'2"-ter-tellurophenes were prepared as potential components of organic metals. Novel dimeric TTF donors linked with conjugative pi electron spacer were synthesized and their properties were studied. The (E) -ethenylene derivative formed high ly conducting CT complexes with TCNQF_4 and DDQ.2,7-Bis (dicyanomethylene) -2,7-dihydrobenzo- [2,1-b : 3,4-b'] dithiophene and - [1,2-b : 4,3-b'] dithiophene and 2,6-bis (dicyanomethylene) -2,6-dihydrobenzo- [1,2-b : 4,5-b'] dithiophene were synthesized as novel electron acceptors bearing a heteroquinoid system.They behave as good electron acceptors comparable to TCNQ and have a small on-site Coulomb energy in their dianion states. 11,11,12,12-Tetracyano-2,6-anthraquinodimethane (TANT) and its 9,10-derivative s were synthesized. All of them are superior electron acceptors with small on-site Coulomb repulsion in the dianion states. The above acceptors afforded many highly conducting CT complexes with typical electron donors. Less

合成了与芘等电子的萘[1,8-bc: 5,4-b'c']和萘[1,8-bc: 4,5-b'c'] -二噻吩作为新的电子给体。以碘和ddq - 2,3,6,7-四噻吩并[1,3-cd: 4,6-c'd']二戊二烯（TBD）为电子给体，合成了与苝等电子给体的CT配合物。TBD具有大致相同的供体能力，并形成了相对高导电性的碘配合物。合成了2-（硫代吡喃-4′-酰基）-1,3-二噻唑的各种取代衍生物和硒类似物作为新的电子给体。对它们的系统研究提供了许多高导电性的CT配合物。合成了吡喃基二甲基和噻吩基二甲基取代呋喃、噻吩和n -甲基吡咯作为有机金属的前驱体。这两种n -甲基吡咯都能与TCNQ形成高导电性的CT配合物。炭疽菌[1,9-cd: 4,10-c'd']和[1,2]二硫代酚类化合物的高导电性。制备了2,2′-铋和2,2′- 5′- 2′-ter-tellurophenes作为有机金属的潜在组分。合成了一种共轭电子间隔层连接的新型二聚TTF给体，并对其性质进行了研究。(E) -乙烯衍生物与TCNQF_4和ddq .2,7-双（二氰亚甲基）-2,7-二氢苯并- [2,1-b: 3,4-b']二噻吩、- [1,2-b: 4,3-b']二噻吩和2,6-双（二氰亚甲基）-2,6-二氢苯并- [1,2-b: 4,5-b']二噻吩形成了高导电性的CT配合物，作为带有杂醌体系的新型电子受体。它们表现为与TCNQ相当的良好电子受体，并且在离子状态下具有小的现场库仑能量。合成了11,11,12,12-四氰-2,6-蒽醌二甲烷（TANT）及其9,10衍生物。它们都是优秀的电子受体，在离子状态下具有较小的现场库仑排斥。上述受体提供了许多具有典型电子给体的高导电性CT配合物。少

项目成果

Masanori FUJII: "Synthesis and Properties of Ethanediylidene-2.2'-bis(5-dicyanomethylene)and Its Dibromo Derivatives as New Extensively Conjugated Electron Acceptors." Synth.Metals. 56/1. 2136-2139 (1993)

Masanori FUJII：“乙二亚基-2.2-双（5-二氰亚甲基）及其二溴衍生物作为新型广泛共轭电子受体的合成和性能。”

Masanori FUJII: "2,6-Bis (dicyanomethylene) -2,6-dihydrobenzo [1,2-b : 4,5-b'] dithiophene as a Novel Electron Acceptors." Synth.Metals. 56/1. 1910-1913 (1993)

Masanori FUJII：“2,6-双（二氰亚甲基）-2,6-二氢苯并[1,2-b：4,5-b]二噻吩作为新型电子受体。”

Tetsuo OTSUBO: "Synthese and Properties of Various Substitution Derivatives of 2-(Thiopyran-4'-ylidene)-1,3-dithiole and Selenium Analogues as Novel Electron Donors." J.Chem.Soc.,Perkin Trans.2. No.12. 1815-1824 (1993)

Tetsuo OTSUBO：“作为新型电子供体的 2-(Thiopyran-4-ylidene)-1,3-dithiole 和硒类似物的各种取代衍生物的合成和性能。”

Tetsuo OTSUBO: "Syntheses,Structure,and Properties of 2,3,6,7-Tetrathiabenzo[1,3-cd:4,6-c'd']dipentalene and Its Methyl,Ethyl,Methylthio,and Ethylthio Derivatives:Novel Fused Polynuclear Heteroarenes." Bull.Chem.Soc.Jpn.66. 2033-2041 (1993)

Tetsuo OTSUBO：“2,3,6,7-四硫苯并[1,3-cd:4,6-cd]二戊二烯及其甲基、乙基、甲硫基和乙硫基衍生物的合成、结构和性质：新颖

Shu YOSHIDA: "Novel Electron Acceptors Bearing a Heteroquinonoid System.4. Syntheses, Properties, and Charge-Transfer Complexes of 2,7-Bis (dicyanomethylene) -2,7-di-hydrobenzo [2,1-b : 3,4-b'] dithiophene, 2,7-Bis (dicyanomethylene) -2,7-dihydrobenzo [1,

Shu YOSHIDA：“带有杂醌类系统的新型电子受体。4. 2,7-双（二氰亚甲基）-2,7-二氢苯并[2,1-b：3,4]的合成、性质和电荷转移配合物