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2-羟基薁-1,3-二羧酸二乙酯与金属醋酸盐和醇盐的反应：金属配合物的形成及酯交换反应

Reaction of Diethyl 2‑Hydroxyazulene-1,3-dicarboxylate with Metal Acetates and Alkoxides: Metal Complex Formation and Transesterification.

作者信息

Iwashina Tatsuya, Hayami Ryohei, Sato Yohei, Sagawa Takuya, Yamamoto Kazuki, Gunji Takahiro

机构信息

Department of Pure and Applied Chemistry, Faculty of Science and Technology, Tokyo University of Science, 2641 Yamazaki, Noda, Chiba 278-8510, Japan.

Department of Industrial Chemistry, Faculty of Engineering, Tokyo University of Science, 6-3-1 Niijuku, Katsushika-ku, Tokyo 125-8585, Japan.

出版信息

ACS Omega. 2025 Aug 25;10(35):39540-39554. doi: 10.1021/acsomega.5c01929. eCollection 2025 Sep 9.

DOI:10.1021/acsomega.5c01929
PMID:40949275
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC12423842/
Abstract

Azulene-embedded heterometallacycles can be handled in air and are expected to have a glossy color derived from the azulenyl ligand. However, very few studies have clearly described the synthesis, structure, and effects of metal species. In this study, the reactions of diethyl 2-hydroxyazulene-1,3-dicarboxylate (DEHA, other abbreviation as H-L) with various metals were investigated to synthesize metal complexes (). were synthesized by the reaction of metal acetates (Pd, Cu, Ni, Co, and Zn acetate) with DEHA and CsCO. Single-crystal X-ray structural analysis showed that and had mononuclear planar and binuclear structures, respectively. In the case of zinc acetate, the formation of a one-dimensional coordination polymer, [ZnCs-(OCH(COOCH))] , was confirmed. For cobalt and nickel acetates, the formation of similar coordination polymers was suggested by mass spectrometry, infrared spectrometry, and energy-dispersive X-ray spectrometry. These complexes were mixed in poly-(methyl methacrylate) (PMMA), and the PMMA composite films exhibited coloration corresponding to the color of the complexes. When DEHA was mixed with titanium tetraisopropoxide and CsCO in an alcohol (PrOH, BuOH, or allyl alcohol), transesterification was observed by nuclear magnetic resonance spectroscopy. This transesterification was necessary for both titanium tetraisopropoxide and CsCO, and a facile transesterification reaction of DEHA was observed for the first time.

摘要

薁嵌入的杂金属环可以在空气中处理，并且预计具有源自薁基配体的光泽颜色。然而，很少有研究清楚地描述金属物种的合成、结构和作用。在本研究中，研究了2-羟基薁-1,3-二羧酸二乙酯（DEHA，其他缩写为H-L）与各种金属的反应，以合成金属配合物（）。通过金属乙酸盐（乙酸钯、乙酸铜、乙酸镍、乙酸钴和乙酸锌）与DEHA和碳酸铯的反应合成了（）。单晶X射线结构分析表明，（）和（）分别具有单核平面结构和双核结构。在乙酸锌的情况下，证实形成了一维配位聚合物[ZnCs-(OCH(COOCH))] 。对于乙酸钴和乙酸镍，通过质谱、红外光谱和能量色散X射线光谱表明形成了类似的配位聚合物。将这些配合物混入聚（甲基丙烯酸甲酯）（PMMA）中，PMMA复合膜呈现出与配合物颜色相对应的着色。当DEHA在醇（丙醇、丁醇或烯丙醇）中与四异丙醇钛和碳酸铯混合时，通过核磁共振光谱观察到酯交换反应。这种酯交换反应对于四异丙醇钛和碳酸铯都是必需的，并且首次观察到DEHA的 facile酯交换反应。

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