Synthesis, structures, and photophysical properties of silicon and carbon-bridged ladder oligo(p-phenylenevinylene)s and related π-electron systems

Yamaguchi, Shigehiro; Xu, Caihong; Yamada, Hiroshi; Wakamiya, Atsushi

doi:10.1016/j.jorganchem.2005.05.019

Cited by 58 publications

(24 citation statements)

References 41 publications

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“…This synthesis methodology was expanded to the synthesis of ladder oligo(pphenylenevinylene)s (LOPVs) and related π-electron systems, having annelated π-conjugated structures with silicon and carbon bridges [89,90]. In this case a combination of two cyclization reactions was applied, i.e., an intramolecular reductive cyclization of (o-silylphenyl)acetylene derivatives and an Friedel-Crafts-type cyclization (Scheme 5).…”

Section: Silicon Analogs Of Oligo(p-phenylenevinylene)smentioning

confidence: 99%

Conjugated Organosilicon Materials for Organic Electronics and Photonics

Ponomarenko

Kirchmeyer

2010

Advances in Polymer Science

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In this chapter different types of conjugated organosilicon materials possessing luminescent and/or semiconducting properties will be described. Such macromolecules have various topologies and molecular structures: linear, branched and hyperbranched oligomers, polymers, and dendrimers. Specific synthetic approaches to access these structures will be discussed. Special attention is devoted to the role of silicon in these structures and its influence on their optical and electrical properties, leading to their potential application in the emerging areas of organic and hybrid electronics.

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Section: Silicon Analogs Of Oligo(p-phenylenevinylene)smentioning

confidence: 99%

Conjugated Organosilicon Materials for Organic Electronics and Photonics

Ponomarenko

Kirchmeyer

2010

Advances in Polymer Science

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“…13 We have been interested in the catalytic syntheses of silole derivatives 14 and the cycloisomerisation of bis-silicon-bridged 1r was envisaged as a method for the synthesis of a bi(1-silaindene). 15 However, the reaction of 1r under conditions similar to those described above led to a totally different outcome: 1,1′,2,2′-tetrahydro-4,4′-bi(1-silanaphthalene) 5 was obtained in 43% yield as the sole product after full conversion of 1r (Scheme 3). The silanaphthalene 5 may have formed through a stitching reaction mediated by a hydroruthenium species in a manner analogous to the path (a) in Scheme 2, but with initial anti-Markovnikov hydroruthenation.…”

Section: Resultsmentioning

confidence: 97%

Ruthenium-catalysed cyclisation reactions of 1,11-dien-6-ynes leading to biindenes

Matsuda

Yonekubo

2020

Org. Biomol. Chem.

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“…[67] 有所不同. 它们的荧光效率和相应碳桥联对-三联苯相当, 这与梯形 π-电子体系中引入硅对其量子效率影响不大 [16] 的结论是一致的. [83] , 这表明其有望作为有机蓝光荧光材料加以利用.…”

Section: Methodsunclassified

Research Progress in Benzosilole-Containing Organic Compounds

Qu¹,

Jiang²,

Chen³

et al. 2014

Chin. J. Org. Chem.

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Benzosilole-containing organic molecules have been potentially applied in opto-electronic material fields, due to their unique structural and optical characteristics. The rigid planar structures of acenes prevent conformational disorder, and extend the π-conjugation. Silacyclopentadiene can form σ*-π* conjugation, lowering the LUMO and enhancing the electron affinity efficiently. In this review, benzosiloles, silicon-bridged stilbene derivatives, silafluorenes and bis-silicon-bridged p-terphenyls are focused on. The recent research progress in the synthesis, modification, properties and applications of benzosilole-containing organic compounds is summarized, and the future research of this field is also prospected. Keywords benzosilole; silicon-bridge; π-conjugated; opto-electronic materials 有机 π-共轭化合物可以作为光电功能材料, 用于制作有机场效应晶体管(OFET) [1 ～ 4] 、有机发光二极管 (OLED) [5-8] 、有机太阳能电池 [9～11] 等诸多光电器件, 而这类材料发展的关键在于新型 π-共轭分子的研发. 其中多并环梯形 π-共轭体系具有许多优点, 如可避免构像无序性、扩大 π-共轭、增强体系荧光特性、提高载流子迁移率 [12～16] 等. 例如: 有机薄膜中并五苯的场效应迁移率达 1.5 cm 2 •V-1 •s-1 , 可以和非晶硅相媲美, 它易形成分子晶体且在低温基质上能形成有序的薄膜 [17] ; 在有机太阳能电池中并五苯可用做 p-型材料, 能量转化效率达 2.7%, 并五苯与 C 60 异质结外量子效率高达 58%, 成为太阳能电池和光电探测器领域极具前景的材料 [18]. 噻咯(Silole)即硅杂环戊二烯, 其硅原子的环外 σ* 轨道与丁二烯的 π*轨道可形成 σ*-π*共轭, 有效降低了体系的 LUMO (Lowest Unoccupied Molecular Orbital, 最低未占轨道)能级, 提高了电子亲合势, 从而利于电子注入和传输 [19～22] , 因此噻咯及其衍生物具有独特的电子结构和光、电性质. 如 2,5-双[6'-(2',2''-二吡啶)]-1,1-二甲基-3,4-二苯基噻咯(PyPySPyPy)的电子迁移率高, 比 OLED 中广泛应用的电子传输材料-三(8-羟基喹啉)铝(Alq 3)提高了近两个数量级 [23]. 同时噻咯还具有较高的固态发光量子效率, 如基于噻咯的有机发光二极管的外量子效率可达 8% [24]. 硅原子对 π-共轭体系的电子结构影响较大, 如噻咯的 LUMO 能级明显低于吡咯、呋喃、噻吩、吡啶, 用噻咯作为构建单元能够得到具有独特电子结构的新型 σ-共轭和 π-共轭分子 [20] .

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Synthesis, structures, and photophysical properties of silicon and carbon-bridged ladder oligo(p-phenylenevinylene)s and related π-electron systems

Cited by 58 publications

References 41 publications

Conjugated Organosilicon Materials for Organic Electronics and Photonics

Conjugated Organosilicon Materials for Organic Electronics and Photonics

Ruthenium-catalysed cyclisation reactions of 1,11-dien-6-ynes leading to biindenes

Research Progress in Benzosilole-Containing Organic Compounds

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