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Issue 35, 2016
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Aluminum alkoxide, amide and halide complexes supported by a bulky dipyrromethene ligand: synthesis, characterization, and preliminary ε-caprolactone polymerization activity

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Abstract

Aluminum halide, alkoxide and amide complexes 2–6 of the form (N,N)AlX2−nYn (n = 0, 1 and (N,N) = 1,9-dimesityl-5-phenyldipyrromethene (1)) were synthesized and characterized by NMR spectroscopy and X-ray crystallography. The in situ generated lithium salt of dipyrromethene 1 was reacted with AlX3 to afford aluminum halide complexes (N,N)AlX2 (X = Cl (2), I (3)) which were isolated as dichroic crystals. Salt metathesis reactions were employed to produce alkoxide complexes (N,N)Al(Cl)(OtBu) (4) and (N,N)Al(OtBu)2 (5) from compound 2. The dimethylamide complex (N,N)Al(NMe2)2 (6) was prepared by reaction of dipyrromethene 1 with [Al(NMe2)3]2. Crystallographic data revealed that the dipyrromethene is non-planar when bulky coligands are present as in compounds 3–6, while in the dichloride complex 2 the dipyrromethene is planar. Halide complexes 2 and 3 reacted with adventitious moisture in toluene to afford crystalline acid–base adducts (N,N)H·HX, (X = Cl (7), I (8)), which adopted structures reminiscent of anion receptors. Alkoxide and dimethylamide complexes 5 and 6 were also applied as precatalysts for the ring-opening polymerization of ε-caprolactone and preliminary results are reported.

Graphical abstract: Aluminum alkoxide, amide and halide complexes supported by a bulky dipyrromethene ligand: synthesis, characterization, and preliminary ε-caprolactone polymerization activity

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Article information


Submitted
18 Jun 2016
Accepted
19 Jul 2016
First published
03 Aug 2016

Dalton Trans., 2016,45, 13787-13797
Article type
Paper

Aluminum alkoxide, amide and halide complexes supported by a bulky dipyrromethene ligand: synthesis, characterization, and preliminary ε-caprolactone polymerization activity

C. G. Gianopoulos, N. Kumar, Y. Zhao, L. Jia, K. Kirschbaum and M. R. Mason, Dalton Trans., 2016, 45, 13787
DOI: 10.1039/C6DT02449A

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