Experimental study reveals decreased sublimation enthalpy in methylated hexaphenylbenzene, suggesting that disrupting specific contacts produces solids with abnormally weak cohesion.
Adding astutely placed methyl groups to hexaphenylbenzene increases molecular weight but simultaneously weakens key C-H···π interactions, thereby leading to decreased enthalpies of sublimation and showing that materials with abnormally weak cohesion can be made by identifying and then obstructing interactions that help control association.
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Maly et al. (2011) studied this question.
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