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共轭三苯胺大环化合物的一锅法合成及其与富勒烯的络合作用

One-pot synthesis of conjugated triphenylamine macrocycles and their complexation with fullerenes.

作者信息

Lu Ying-Bo, Kanehashi Shinji, Minegishi Kazushi, Wang Shu-Ping, Cheng Jin, Ogino Kenji, Li Shijun

机构信息

Graduate School of Bio-Applications and Systems Engineering, Tokyo University of Agriculture and Technology 2-24-16 Nakacho, Koganei Tokyo 184-8588 Japan

College of Material, Chemistry and Chemical Engineering, Hangzhou Normal University Hangzhou 311121 P. R. China

出版信息

RSC Adv. 2021 Oct 12;11(53):33431-33437. doi: 10.1039/d1ra06200j. eCollection 2021 Oct 8.

DOI:10.1039/d1ra06200j
PMID:35497513
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC9042278/
Abstract

Triphenylamine derivates have been utilized as building blocks in hole-transporting materials. Herein, we describe the synthesis of three octyl-derived conjugated triphenylamine macrocycles with different sizes, and a 4-(2-ethylhexyloxy)-substituted cyclic triphenylamine hexamer using a palladium-catalyzed C-N coupling reaction. These conjugated triphenylamine macrocycles not only have interesting structures, but also are capable of complexing with C, C and PCBM. Their binding stoichiometries with fullerenes were all determined to be 1 : 1 by an emission titration method. The association constants of these complexes were measured to be in the range of 0.115-1.53 × 10 M depending on the cavity size of the triphenylamine macrocycles and the volume of the fullerenes. The space-charge-limited current properties of the complexes were further investigated using the fabricated ITO/PEDOT:PSS/active layer/Au devices.

摘要

三苯胺衍生物已被用作空穴传输材料的构建单元。在此，我们描述了三种不同尺寸的辛基衍生共轭三苯胺大环化合物以及一种使用钯催化的C-N偶联反应合成的4-(2-乙基己氧基)取代的环状三苯胺六聚体的合成方法。这些共轭三苯胺大环化合物不仅具有有趣的结构，而且能够与C、C和PCBM络合。通过发射滴定法确定它们与富勒烯的结合化学计量比均为1∶1。根据三苯胺大环化合物的空腔大小和富勒烯的体积，测得这些配合物的缔合常数在0.115 - 1.53×10 M范围内。使用制备的ITO/PEDOT:PSS/活性层/Au器件进一步研究了这些配合物的空间电荷限制电流特性。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4cd9/9042278/640a898d7f46/d1ra06200j-f4.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4cd9/9042278/6329cba97020/d1ra06200j-s1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4cd9/9042278/9d9339017bdc/d1ra06200j-s2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4cd9/9042278/a73538266d36/d1ra06200j-f1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4cd9/9042278/d40a85d8202f/d1ra06200j-f2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4cd9/9042278/97a5175d1fc8/d1ra06200j-f3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4cd9/9042278/640a898d7f46/d1ra06200j-f4.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4cd9/9042278/6329cba97020/d1ra06200j-s1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4cd9/9042278/9d9339017bdc/d1ra06200j-s2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4cd9/9042278/a73538266d36/d1ra06200j-f1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4cd9/9042278/d40a85d8202f/d1ra06200j-f2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4cd9/9042278/97a5175d1fc8/d1ra06200j-f3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4cd9/9042278/640a898d7f46/d1ra06200j-f4.jpg

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