<i>N</i>-(2-(Diphenylphosphino)ethyl)-2-alkyl-5,6,7,8-tetrahydro-quinolin-8-amines iron(<scp>ii</scp>) complexes: structural diversity and the ring opening polymerization of ε-caprolactone

Wang, Yun; Zhang, Wenjuan; Wang, Xing; Zuo, Weiwei; Xue, Xiaopan; Ma, Yanping; Sun, Wen-Hua

doi:10.1039/d3ra05867k

RSC Adv.

2023

DOI: 10.1039/d3ra05867k

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N-(2-(Diphenylphosphino)ethyl)-2-alkyl-5,6,7,8-tetrahydro-quinolin-8-amines iron(ii) complexes: structural diversity and the ring opening polymerization of ε-caprolactone

Yun Wang,

Wenjuan Zhang,

Xing Wang

et al.

Abstract: A series of 2-alkylated N-(2-(diphenylphosphino)ethyl)-5,6,7,8-tetrahydro-quinolin-8-amines-iron(ii), activated with LiCH2SiMe3, efficiently initiated the ROP of ε-caprolactone with TOF up to 8.8 × 103 h−1, producing PCL within 9.21–24.3 × 104 g mol−1.

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Cited by 3 publications

References 75 publications

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Efficient ring-opening polymerization of epsilon-caprolactone catalyzed by iron(III) chloride under mild reaction conditions

Wu,

Zhou,

Zhou

et al. 2023

J Polym Res

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As a biodegradable polyester, the commercialized synthesis protocol of poly(ε-caprolactone) (PCL) under mild conditions is of great signi cance and attractive. Herein, the ring-opening polymerization (ROP) of εcaprolactone (ε-CL) using FeCl 3 catalyst and benzyl alcohol (BnOH) as the initiator was developed. FeCl 3 has been proved to be an e cient catalyst for the ROP of ε-CL under mild conditions. The conversion of ε-CL to PCL was 98.8% at 60 o C within 4 h, with number-average molecular weight (Mn) and dispersity (PDI) of 16500 g/mol and 1.28, respectively. Moreover, a coordination-insertion ring-opening polymerization mechanism mediated by FeCl 3 was proposed. Overall, this work is expected to provide a feasible industrial method for the preparation of PCL from the direct aerobic oxidation of cyclohexanone.

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Efficient ring-opening polymerization of epsilon-caprolactone catalyzed by iron(III) chloride under mild reaction conditions

Wu,

Zhou,

Zhou

et al. 2023

J Polym Res

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Anilido-Oxazoline-Ligated Iron Alkoxide Complexes for Living Ring-Opening Polymerization of Cyclic Esters with Controllability

Pan,

Hao,

et al. 2024

Inorg. Chem.

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Ring-Opening Homo- and Copolymerization of Cyclic Esters Catalyzed by Iron(III) Triflate

Nakayama,

Omori,

Tanaka

et al. 2024

Catalysts

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Biomass-based and biodegradable poly(l-lactide) (PLLA) is synthesized by ring-opening polymerization of l-lactide (LLA), for which tin(II) 2-ethylhexanoate is a major catalyst. However, the potential toxicity of tin can be a problem, especially in biomedical applications. In this study, we focused on iron, which is a non-toxic metal and an abundant resource. We investigated the ring-opening homo- and copolymerization of cyclic esters such as LLA and ε-caprolactone (CL) catalyzed by iron(III) triflate, Fe(OTf)3, which is commercially available and known as a Lewis acid. In the polymerization of LLA in toluene at 110 °C, Fe(OTf)3 showed relatively high activity and yielded PLLA with unimodal molecular weight distribution. The addition of 1,8-bis(dimethylamino)naphthalene (proton sponge: PS) to the Fe(OTf)3 catalyst system increased the yield and molecular weight of the resulting polymer. In contrast, the polymerization of CL by Fe(OTf)3 was decelerated by the presence of PS. The Fe(OTf)3 system was found to have an exceptionally high preference for CL over LLA in the copolymerization of LLA and CL, with the reactivity ratio of rLLA = 0.51 and rCL = 6.9. In contrast, the Fe(OTf)3–2PS system exhibited an LLA preference with rLLA = 15 and rCL = 0.22, indicating that the comonomer selectivity changed depending on the presence or absence of PS. While the LLA polymerization rate by the Fe(OTf)3 system showed a second-order dependence on the Fe(OTf)3 concentration, that of the Fe(OTf)3–PS system showed a first-order dependence on the Fe(OTf)3–PS concentration.

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N-(2-(Diphenylphosphino)ethyl)-2-alkyl-5,6,7,8-tetrahydro-quinolin-8-amines iron(ii) complexes: structural diversity and the ring opening polymerization of ε-caprolactone

Abstract: A series of 2-alkylated N-(2-(diphenylphosphino)ethyl)-5,6,7,8-tetrahydro-quinolin-8-amines-iron(ii), activated with LiCH2SiMe3, efficiently initiated the ROP of ε-caprolactone with TOF up to 8.8 × 103 h−1, producing PCL within 9.21–24.3 × 104 g mol−1.

Cited by 3 publications

References 75 publications

Efficient ring-opening polymerization of epsilon-caprolactone catalyzed by iron(III) chloride under mild reaction conditions

Efficient ring-opening polymerization of epsilon-caprolactone catalyzed by iron(III) chloride under mild reaction conditions

Anilido-Oxazoline-Ligated Iron Alkoxide Complexes for Living Ring-Opening Polymerization of Cyclic Esters with Controllability

Ring-Opening Homo- and Copolymerization of Cyclic Esters Catalyzed by Iron(III) Triflate

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