Cyclodextrin Complexes of Bisepoxide and of α,ω-Diamine in Several Molar Ratios. Preparation and Characterization in the Solid State

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Abstract
Addition of 1,4-butanediol diglycidyl ether (glycidyl = 2,3-epoxypropyl) to aqueous solutions of α-cyclodextrin (CD) leads to separation of the 2 : 1 complex from the solution. The 13C CP/MAS NMR spectrum of the complex indicates the presence of diastereomeric oxirane groups formed via the complexation. 1,4-Butanediol diglycidyl ether forms the 1 : 1 or 2 : 2 complex with γ-CD similarly from the aqueous reactions of the two compounds. 2,2-Dimethyltrimethylene glycol diglycidyl ether also forms water-insoluble host–guest complexes with α-CD (2 : 1) and with γ-CD (1 : 1 or 2 : 2). Poly(propylene glycol diglycidyl ether) with an Mn of 640 reacts with β-CD to give the 1 : 4 complex. Poly(tetrahydrofuran) terminated with NH2 groups at both ends also forms the 1 : 4 complexes both with α-CD and with γ-CD.