Synthesis of amphiphilic chiral salen complexes and their conformational manipulation at the air–water interface,Dalton Transactions

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Synthesis of amphiphilic chiral salen complexes and their conformational manipulation at the air–water interface
Dalton Transactions ( IF 3.5 ) Pub Date : 2022-11-10 , DOI: 10.1039/d2dt03201e
Shigehisa Akine _{1,

2} , Keisuke Nomura ₂ , Mizuho Takahashi ₂ , Yoko Sakata _{1,

2} , Taizo Mori _{3,

4} , Waka Nakanishi ₃ , Katsuhiko Ariga _{3,

4}

Affiliation

A series of amphiphilic salen complexes, [L^1a,bM] and [L^2a,bM], were designed and synthesized. These complexes consist of two or four hydrophilic triethylene glycol (TEG) chains and a hydrophobic π-extended metallosalen core based on naphthalene or phenanthrene. The obtained amphiphilic complexes, [L^1bM] (M = Ni, Cu, Zn), formed a monolayer at the air–water interface, while the monocationic [L^1bCo(MeNH₂)₂](OTf) did not form a well-defined monolayer. The number of hydrophilic TEG chains also had an influence on the monolayerformation behavior; the tetra-TEG derivatives, [L^1bNi] and [L^2bNi], showed a pressure rise at a less compressed region than the bis-TEG derivatives, [L^1aNi] and [L^2aNi]. In addition, the investigation of their compressibility and compression modulus suggested that the tetra-TEG derivatives, [L^1bNi] and [L^2bNi], are more flexible than the corresponding bis-TEG analogues, [L^1aNi] and [L^2aNi], and that the phenanthrene derivatives [L^1a,bNi] were more rigid than the corresponding naphthalene analogues, [L^2a,bNi]. The Langmuir–Blodgett (LB) films of one of the complexes, [L^1bNi], showed CD spectra slightly different from that in solution, which may originate from the unique anisotropic environment of the air–water interface. Thus, we demonstrated the possibility of controlling the chiroptical properties of metal complexes by mechanical compression.

中文翻译：

两亲性手性 salen 配合物的合成及其在气水界面的构象操作

设计并合成了一系列两亲性 salen 配合物，[ L ^1a,b M] 和 [ L ^{2a,b M]。}这些复合物由两个或四个亲水性三甘醇 (TEG) 链和一个基于萘或菲的疏水性 π 扩展金属沙仑核组成。获得的两亲复合物 [ L ^1b M] (M = Ni, Cu, Zn) 在空气-水界面形成单分子层，而单阳离子 [ L ^1b Co(MeNH ₂ ) ₂ ](OTf) 不形成单分子层定义明确的单层。亲水性 TEG 链的数量也对单层形成行为有影响；四 TEG 衍生物，[ L ^1b Ni] 和 [L ^2b Ni]，与双 TEG 衍生物 [ L ^1a Ni] 和 [ L ^2a Ni] 相比，在压缩较小的区域显示出压力升高。此外，对其压缩率和压缩模量的研究表明，四 TEG 衍生物 [ L ^1b Ni] 和 [ L ^2b Ni] 比相应的双 TEG 类似物 [ L ^1a Ni] 和 [ L ^2a Ni]，并且菲衍生物 [ L ^1a,b Ni] 比相应的萘类似物 [ L ^2a,b你]。其中一种配合物 [ L ^1b Ni] 的 Langmuir-Blodgett (LB) 薄膜显示出与溶液中的 CD 光谱略有不同，这可能源于空气-水界面独特的各向异性环境。因此，我们证明了通过机械压缩控制金属配合物手性的可能性。

更新日期：2022-11-14

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