Towards the Preparation of Electrochromic Materials with Strong Absorption in the Near-Infrared Region: Synthesis and Redox Behavior of Azulene-Substituted Enediyne Scaffolds Connected by a 9,10-Anthracenediyl Spacer
Towards the Preparation of Electrochromic Materials with Strong Absorption in the Near-Infrared Region: Synthesis and Redox Behavior of Azulene-Substituted Enediyne Scaffolds Connected by a 9,10-Anthracenediyl Spacer
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近红外区强吸收电致变色材料的制备：9,10-蒽二基间隔基连接的薁取代烯二炔支架的合成和氧化还原行为
DOI：
10.1002/ejoc.200900743
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发表时间：
2009
影响因子：
2.8
通讯作者：
N. Morita
中科院分区：
文献类型：
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作者：
S. Ito;T. Iida;J. Kawakami;T. Okujima;N. Morita
通过pd催化6-卤代氮杂烯7b和7c与烯二炔衍生物6的重复炔化反应，制备了以9,10-蒽二基间隔物作为氧化还原活性亚结构连接的烯二炔支架，其外围的6-氮杂烯基为π电子接受基团（3a和3b）。在循环伏安法（CV）上，azulene-取代的双（烯二炔）3a和3b表现出两种可逆的一步双电子还原性质，这可归因于重阴离子和四阴离子的形成。3a和3b的电化学还原在近红外区产生了强吸收，形成了稳定的重阴离子3aRED2 -和3bRED2 -。电致变色分析表明，虽然CV具有良好的可逆性，但四阴离子3aRED4 -··和3bRED4 -··的稳定性较低。还制备了单烯二炔体系11a和11b进行比较。11a和11b的电化学还原没有表现出良好的电化学可逆性，但电化学还原在近红外区产生了很强的吸收，类似于双烯二炔体系中稳定的重阴离子物质3aRED2 -和3bRED2 -的形成。（©Wiley-VCH Verlag GmbH & Co. KGaA，德国Weinheim 69451, 2009）
Enediyne scaffolds connected by a 9,10-anthracenediyl spacer as a redox-active substructure with 6-azulenyl groups as π-electron-accepting groups in their periphery (3a and 3b) have been prepared by a one-pot reaction involving repeated Pd-catalyzed alkynylation of 6-haloazulenes 7b and 7c with bis(enediyne) derivative 6. The azulene-substituted bis(enediyne)s 3a and 3b exhibited two reversible one-step, two-electron reduction properties upon cyclic voltammetry (CV) attributable to the formation of dianionic and tetraanionic species. The electrochemical reduction of 3a and 3b led a strong absorption in the near-IR region corresponding to the formation of the stabilized dianionic species 3aRED2– and 3bRED2–. An electrochromic analysis revealed the lower stability of the tetraanionic species 3aRED4–·· and 3bRED4–··, although the CV exhibited good reversibility. The mono(enediyne) systems 11a and 11b were also prepared for comparison. The electrochemical reduction of 11a and 11b did not exhibit good electrochemical reversibility by CV, but the electrochemical reduction led to a strong absorption in the near-IR region, similar to the formation of the stabilized dianionic species 3aRED2– and 3bRED2– in the bis(enediyne) systems. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)
烯二炔支架作为氧化还原活性发色团的电致变色应用。
DOI：
--
发表时间：
2004
期刊：
European Journal of Organic Chemistry 8号
影响因子：
--
作者：
S.Ito;M.Ando;A.Nomura;N.Morita;C.Kabuto;H.Mukai;K.Ohta;J.Kawakami;A.Yoshizawa;A.Tajiri;伊東 俊司;伊東 俊司
通讯作者：
伊東 俊司