Precision synthesis of 3-substituted urushiol analogues and the realization of their urushiol-like performance.
Precision synthesis of 3-substituted urushiol analogues and the realization of their urushiol-like performance.
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3-取代漆酚类似物的精密合成及其类漆酚性能的实现
作者：
漆酚是一种资源有限的天然涂层材料，具有多种应用;然而，漆酚类似物的合成和实现其漆酚样性能仍然具有挑战性。以邻苯二酚与甲醛和N-叔丁氧羰基哌嗪的Mannich反应为关键步骤，采用两步法合成了4种漆酚类似物3-（（4-烯酰基哌嗪-1-基）甲基）邻苯二酚，其结构与漆酚类似。通过使用优化，可以获得操作方便，成本效益和可扩展性的优点。这些类似物在铜上的电聚合被发现是实用的，由于它们比漆酚更高的有氧稳定性，提供具有期望的硬度、粘附强度、疏水性和热稳定性的坚固涂层。此外，涂层表现出有效的防腐蚀保护铜的初始防腐蚀效率高达99.9%，并在3.5wt%NaCl溶液中浸泡4周后，相对较高的效率（大于97%）。电化学和红外光谱表征数据表明，电聚合过程涉及苯氧基自由基与自身和C
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由potrace 1.16创建，由Peter Selinger编写2001-2019
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侧链中的C键，形成坚固的交联涂层。本工作为高性能漆酚类似物的合成及作为金属防护材料的潜在应用奠定了基础。
Urushiol is a resource-limited natural coating material with diverse applications; however, the synthesis of urushiol analogues and the realization of their urushiol-like performance remain challenging. Herein, four urushiol analogues, namely, 3-((4-alkenoylpiperazin-1-yl)methyl)catechols with the precise 3-substitution pattern on a catechol as that found in urushiol were synthesized by employing the Mannich reaction of catechol with formaldehyde and N-Boc-piperazine as the key step in a two-step route. By using optimization, the advantages of convenience in operation, cost-effectiveness, and scalability could be obtained. The electropolymerization of these analogues on copper was found to be practical due to their higher aerobic stability than urushiol, affording robust coatings with desirable hardness, adhesion strength, hydrophobicity, and thermal stability. Furthermore, the coatings exhibited effective corrosion protection on copper with initial anticorrosion efficiency up to 99.9% and comparatively higher efficiency (more than 97%) after 4 weeks of immersion in 3.5 wt% NaCl solution. The evidence from the electrochemical and infrared spectroscopic characterization data revealed that the electropolymerization process mechanically involved the free radical coupling of phenoxyl radicals to themselves and to the C
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Created by potrace 1.16, written by Peter Selinger 2001-2019
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C bonds in the side chain, forming a robust crosslinking coating. This work paves a way for the synthesis of high-performance urushiol analogues with potential applications as metal protection materials.
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影响因子：
4.7
作者：
Watanabe, Hirohmi;Takahashi, Mariko;Yoshida, Masaru
通讯作者：
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影响因子：
6.1
作者：
Lu, Rong;Kamiya, Yukio;Miyakoshi, Tetsuo
通讯作者：
Miyakoshi, Tetsuo
影响因子：
5.5
作者：
Tsujimoto, T;Uyama, H;Kobayashi, S
通讯作者：
Kobayashi, S
影响因子：
3.6
作者：
LOEV, B;DAWSON, CR
通讯作者：
DAWSON, CR
影响因子：
2.5
作者：
Rosero-Navarro, N. C.;Pellice, S. A.;Aparicio, M.
通讯作者：
Aparicio, M.