Synthesis and grafting properties of functionalized oligo(para‐phenylene)s

Synthesis and grafting properties of functionalized oligo(para‐phenylene)s
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功能化低聚(对亚苯基)的合成及接枝性能

DOI:
10.1002/(sici)1521-3935(19980401)199:4
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发表时间:
1998
影响因子:
2.5
通讯作者:
B. François
B. François
中科院分区:
化学4区
文献类型:
--
作者:
L. Si;F. Nüesch;L. Zuppiroli;B. François

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为了将共轭分子接枝到金属或氧化物电极上(这是迈向可靠的新一代有机发光二极管的关键一步),我们通过阴离子聚合合成了可溶性低聚环己二烯(12个环单元),并用羧酸、硫醇和硅氧烷对它们进行了官能化。低聚物芳构化为低聚(对苯基)(OPP)是通过与氯苯腈脱氢进行的。用溶液平衡法研究了羧基低聚(对苯撑)衍生物在氧化铟锡粉末上的吸附。四氢呋喃在四氢呋喃中的平衡常数K=2 15 0 0l.mol-1,最大表面覆盖率(Nmax)为4μmol/m2。由吸附的低聚对苯撑的表面密度推算出每个分子的特征面积为40A2,这表明形成了密集堆积的垂直吸附分子单分子层。
For the purpose of grafting conjugated molecules on metal or oxide electrodes (which is an essential step towards a new generation of reliable organic light emitting diodes), we have synthesized soluble oligocyclohexadienes (12 cyclic units) by anionic polymerization and functionalized them by carboxylic acids, thiol and siloxane. Aromatization of the oligomer to oligo(para-phenylene) (OPP) is carried out by dehydrogenation with chloranil. The adsorption of the carboxylic oligo(para-phenylene) derivatives on indium tin oxide powder is investigated by solution equilibration. In tetrahydrofuran (THF) an equilibrium constant of K = 21 500 l.mol -1 and a maximum surface coverage (N max ) of 4 μmol/m 2 are obtained by using the Langmuir equation. A characteristic area of 40 A 2 per molecule is inferred from the surface density of adsorbed oligo(para-phenylene), which indicates that a densely packed monolayer of vertically adsorbed molecules is formed.