Synthesis and Characterization of Azadipyrromethene-alt-p-Phenylene Ethynylene Conjugated Polymers and Their Chelates

Synthesis and Characterization of Azadipyrromethene-alt-p-Phenylene Ethynylene Conjugated Polymers and Their Chelates
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氮杂二吡咯亚甲基-替代-对亚苯基亚乙炔基共轭聚合物及其螯合物的合成与表征

DOI:
10.1021/ma301399x
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发表时间:
2012
期刊:
影响因子:
5.5
通讯作者:
G. Sauvé
G. Sauvé
中科院分区:
化学1区
文献类型:
--
作者:
Lei Gao;Saide Tang;Lei Zhu;G. Sauvé

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通过双碘(四苯基氮杂二吡咯亚甲基)与1,4-双((2-乙基己基)氧基)-2,5-二乙炔基苯的Sonogashira偶联合成了几种在主链中掺入氮杂二吡咯亚甲基(aza-DIPY)染料的n型共轭聚合物。与我们之前报道的十二烷基烷氧基相比,在二乙炔基苯共聚单体上使用支链烷氧基产生的聚合物具有更高的分子量和在有机溶剂中更高的溶解度。通过后聚合反应将氮杂-DIPY 部分与 BF2、Cu(I)PEt3 或 Ag(I)PEt3 配位,进一步调节这些聚合物的物理性质。与未螯合前体相比,与缺电子 BF2 配位可提高其在有机溶剂中的溶解度、更高的电子亲和力(~4.5 eV)、更低的 LUMO 能级(<-5.6 eV)和更低的光学带隙(<1.34 eV)。与富电子的 Cu(I) 和 Ag(I) 金属的配位导致更高的光学带隙 (1.5 eV) 以及更高的 HOMO (-5.3 eV) 和 LUMO (-4.0 eV) 能级。 X-r...
Several n-type conjugated polymers incorporating azadipyromethene (aza-DIPY) dyes in the main chain were synthesized by Sonogashira coupling of bisiodo(tetraphenylazadipyrromethene)s with 1,4-bis((2-ethylhexyl)oxy)-2,5-diethynylbenzene. Using branched alkoxy groups on the diethynylbenzene comonomer resulted in polymers with higher molecular weight and higher solubility in organic solvents than our previous report with dodecylalkoxy groups. The physical properties of these polymers were further tuned by coordination of the aza-DIPY moiety with BF2, Cu(I)PEt3, or Ag(I)PEt3 via a postpolymerization reaction. Coordination with the electron-deficient BF2 resulted in improved solubility in organic solvents, higher electron affinity (∼4.5 eV), lower LUMO energy levels (<−5.6 eV), and lower optical bandgaps (<1.34 eV) than the unchelated precursor. Coordination with the electron-rich Cu(I) and Ag(I) metals resulted in higher optical bandgaps (1.5 eV) and higher HOMO (−5.3 eV) and LUMO (−4.0 eV) energy levels. X-r...
DOI: 10.1021/ol8018506
发表时间: 2008-11-06
期刊: ORGANIC LETTERS
影响因子: 5.2
作者:
Loudet, Aurore;Bandichhor, Rakeshwar;Burgess, Kevin;Palma, Aniello;McDonnell, Shane O.;Hall, Michael J.;O'Shea, Donal F.
通讯作者: O'Shea, Donal F.