一种具有四环核心的新型噻吩稠合多环芳烃：合成、表征、光学和电化学性质。

A novel thiophene-fused polycyclic aromatic with a tetracene core: synthesis, characterization, optical and electrochemical properties.

机构信息

College of Science and Technology, Nihon University, Narashinodai, Funabashi, Chiba 2748501, Japan.

出版信息

Molecules. 2011 May 27;16(6):4467-81. doi: 10.3390/molecules16064467.

DOI:10.3390/molecules16064467

PMID:21623316

原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC6264305/

Abstract

FeCl₃-mediated oxidative cyclization was successfully used to construct an extended thiophene-pendant pyrene skeleton and synthesize a novel thiophene-fused polycyclic aromatic (THTP-C) with a tetracene core. The identity of the compound was confirmed by ¹H-NMR, ¹³C-NMR, MS, and elemental analysis. Meanwhile, a single crystal of THTP-C was obtained and analyzed by X-ray single-crystal diffraction. THTP-C has a "saddle" shaped π-conjugated 1-D supramolecular structure, and favors highly ordered self-assembly by π-π interactions as evidenced by its concentration-dependent ¹H-NMR spectra in solution. The optical properties of THTP-C were investigated by ultraviolet-visible (UV-Vis) and photoluminescence (PL) spectroscopy and its electrochemical properties were investigated by cyclic voltammetry (CV). The relatively large band gap (2.86 eV), low E(HOMO) level (-5.64 eV) and intermolecular π-π interactions imply that THTP-C has a high stability against photo-degradation and oxidation, and may be a promising candidate for stable hole-transporting materials.

摘要

三氯化铁介导的氧化环化反应成功地用于构建扩展的噻吩-并苯并芘骨架，并合成了一种具有四并苯核心的新型噻吩稠合多环芳烃（THTP-C）。通过 ¹H-NMR、¹³C-NMR、MS 和元素分析确认了化合物的结构。同时，获得了 THTP-C 的单晶，并通过 X 射线单晶衍射进行了分析。THTP-C 具有“鞍形”π 共轭 1-D 超分子结构，并且通过 π-π 相互作用有利于高度有序的自组装，这可以通过其在溶液中的浓度依赖性 ¹H-NMR 光谱得到证明。通过紫外可见（UV-Vis）和光致发光（PL）光谱研究了 THTP-C 的光学性质，并通过循环伏安法（CV）研究了其电化学性质。较大的能隙（2.86 eV）、低 HOMO 能级（-5.64 eV）和分子间的 π-π 相互作用表明，THTP-C 具有很高的光降解和氧化稳定性，可能是一种有前途的稳定空穴传输材料。