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Polyhedral oligomeric silsesquioxanes (POSSs), Am-POSS(x,y) , prepared by hydrolytic condensation, contains two types of ammonium side-chain groups, where the numbering of x and y represents the type of ammonium ions in the POSS structure, corresponding to primary ( 1 ), secondary ( 2 ), tertiary ( 3 ), and quaternary ( 4 ) ammonium ions. Mixtures of the two starting materials selected from organotrialkoxysilanes containing primary, secondary, and tertiary amines and a quaternary ammonium salt [(RO) 3 Si(CH 2 ) 3 R', R = CH 3 or CH 2 CH 3 , R' = NH 2 , NHCH 3 , N(CH 3 ) 2 , and N(CH 3 ) 3 Cl] were dissolved in dimethyl sulfoxide (DMSO). The hydrolytic condensation was performed in the presence of bis(trifluoromethansulfonyl)imide (HNTf 2 ) and water. All Am-POSS(x,y) structures consisted of a cage-type octamer (T 8 -POSS), as confirmed by 29 Si NMR spectrometry and matrix-assisted laser desorption ionization-time of flight mass spectrometry (MALDI-TOF MS). Differential scanning calorimetry (DSC) and X-ray diffraction (XRD) analyses indicated that Am-POSS(1,3) , Am-POSS(1,4) , and Am-POSS(2,4) had amorphous structures. These POSSs have two or three differences in the number of methyl groups between the two types of ammonium side-chains. Conversely, Am-POSS(1,2) , Am-POSS(2,3) , and Am-POSS(3,4) had crystalline structures. The difference in the number of methyl groups between the two types of ammonium side-chains in these POSSs is only one. Therefore, the crystalline-amorphous structure of Am-POSS(x,y) is controlled by the side-chain group combinations. Furthermore, Am-POSS(1,3) , Am-POSS(1,4) , and Am-POSS(2,4) are protic ionic liquids with relatively low flow temperatures.

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Control of Crystalline-Amorphous Structures of Polyhedral Oligomeric Silsesquioxanes Containing Two Types of Ammonium Side-Chain Groups and Their Properties as Protic Ionic Liquids