Effect of Self-Association on the Phase Stability of Triphenylamine Derivatives

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• 作者：Carlos F. R. A. C. Lima ; Jos茅 C. S. Costa ; Andr茅 Melo ; Hil谩rio R. Tavares ; Artur M. S. Silva ; Lu谋虂s M. N. B. F. Santos
• 刊名：Journal of Physical Chemistry A
• 出版年：2015
• 出版时间：June 25, 2015
• 年：2015
• 卷：119
• 期：25
• 页码：6676-6682
• 全文大小：388K
• ISSN：1520-5215

文摘

The self-association equilibrium, i.e. formation of noncovalent dimers, in two triphenylamine derivatives, TPD (N,N鈥?bis(3-methylphenyl)-N,N鈥?diphenylbenzidine) and mMTDAB (1,3,5-tris[(3-methylphenyl)phenylamino]benzene), in solution was evaluated by ¹H NMR spectroscopy. The gas-phase energetics of the respective dimerization processes was explored by computational quantum chemistry. The results indicate that self-association is significantly more extensive in TPB than in TDAB. It is proposed that this fact helps to explain why TPB presents a stability higher than expected in the liquid phase, which is reflected in a lower melting temperature, a less volatile liquid, and possibly a higher tendency to form a glass. These results highlight the influence of self-association on the phase equilibria and thermodynamic properties of pure organic substances.