From Step-Saving New Synthesis to Photovoltaic Applications of Triindenotrithiophene (TITT) and Related π-Extended Oligoaryls.

IF 3.5 3区化学 Q2 CHEMISTRY, MULTIDISCIPLINARY

Chemistry - An Asian Journal Pub Date : 2025-03-17 DOI:10.1002/asia.202401830

Yin-Chi Wang, Kun-Mu Lee, Chen-Yu Weng, Shan-Ru Lin, Ching-Yuan Liu

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Abstract

Truxenes, the π-conjugated small molecules with a C_3h-symmetry, have been extensively investigated in synthesis and application as organic optoelectronic materials. Compared to truxenes, triindenotrithiophene (TITT), a thienyl congener of truxene, was much less explored in the field of synthetic chemistry as well as photovoltaic applications. Different from the reported synthesis requiring at least 14 steps to access TITT-related small molecules, in this work, we have successfully developed a seven-step new synthetic route to TITT and its π-extended oligoaryls (YCW01-04). Our synthetic strategy involved two direct C─H/C─Br coupling reactions, avoiding tedious protection/deprotection chemical transformations. Essential reaction conditions including ligand, base, and solvent for direct C─H arylations were well-optimized, thus affording target products in yields up to 87% (YCW02). In addition, for the first time, the TITT core-based oligoaryls were fabricated as hole-transporting material (HTM) in perovskite solar cells (PSC), giving the highest power conversion efficiency (PCE) of 15.3% (YCW01).

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从节省步骤的新合成到三吲哚三噻吩（TITT）及其相关的π延伸低聚芳基的光伏应用。

Truxenes是一种具有c3h对称性的π共轭小分子，作为有机光电材料在合成和应用方面得到了广泛的研究。与truxenes相比，tritininotrithiphene （TITT）是truxene的噻基同系物，在合成化学和光伏应用领域的研究较少。不同于以往报道的至少需要14步才能获得TITT相关小分子的合成方法，本研究成功开发了一条7步合成TITT及其π扩展寡聚芳基（YCW01-04）的新途径。我们的合成策略包括两个直接的C-H/C-Br偶联反应，避免了繁琐的保护/去保护化学转化。优化了C-H直接芳化反应的基本条件，包括配体、碱和溶剂，从而获得了产率高达87%的目标产物（YCW02）。此外，首次在钙钛矿太阳能电池（PSC）中制备了TITT核基低聚羰基作为空穴传输材料（HTM），其功率转换效率（PCE）最高，为15.3% （YCW01）。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

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来源期刊

Chemistry - An Asian Journal 化学-化学综合

CiteScore

7.00

自引率

2.40%

发文量

535

审稿时长

1.3 months

期刊介绍： Chemistry—An Asian Journal is an international high-impact journal for chemistry in its broadest sense. The journal covers all aspects of chemistry from biochemistry through organic and inorganic chemistry to physical chemistry, including interdisciplinary topics. Chemistry—An Asian Journal publishes Full Papers, Communications, and Focus Reviews. A professional editorial team headed by Dr. Theresa Kueckmann and an Editorial Board (headed by Professor Susumu Kitagawa) ensure the highest quality of the peer-review process, the contents and the production of the journal. Chemistry—An Asian Journal is published on behalf of the Asian Chemical Editorial Society (ACES), an association of numerous Asian chemical societies, and supported by the Gesellschaft Deutscher Chemiker (GDCh, German Chemical Society), ChemPubSoc Europe, and the Federation of Asian Chemical Societies (FACS).