Benzimidazolene-2-thiones: A New Class of Molecules for the Engineering of Molecular Tapes in the Organic Solid State

Chemistry of Materials

Volumn 9, Issue 9, 1997, Pages 1954-1961

  Simanek, Eric E ^a   Tsoi, Anne ^a   Wang, Clay C C ^a   Whitesides, George M ^a   McBride, Mary T ^b   Tayhas, G ^b   Palmore, R ^b  

^a HARVARD UNIVERSITY   (United States)

^b UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000061352     PISSN: 08974756     EISSN: None     Source Type: Journal    
DOI: 10.1021/cm960443v     Document Type: Article

References (33)

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22. The greatest advantage of these compounds over any others that we have studied (2-benzimidazolones, diketopiperazines, barbituric acid·melamine cocrystals) is their high solubility in many organic solvents. This solubility allows us to use conventional silica gel chromatography to purify the products and intermediates and gives us an opportunity to survey many different solvents for crystallization. Crystallization of the benzimidazolones is limited to only a few high boiling solvents including DMF and N-methylpyrolidinone which evaporate very slowly under ambient conditions. We hypothesized that the greater diversity in solvent choice might translate into both a greater chance for success of crystallization, and an opportunity for a more rigorous search for polymorphs.
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29. 2 have been observed to change from translucent, high-quality crystals to dried powders.
30. For a tabulation of hydrogen bond strengths for a variety of organic molecules see: Leahy, D. E.; Morris, J. J.; Taylor, P. J.; Wait, A. R. J. Chem. Soc., Perkins Trans. 2 1992, 705 and references therein.
31. Similarities between other powder patterns can be made, but their validity is questionable. For example: 1-SMe and 1-SCl may pack as tapes with similar structures. Three important similarities exist in the XPD traces of 1-SMe and 1-SCl and those of parallel tapes: all show one line between 9° and 10°; one line at 14° (present in 1-SCl, but difficult to see in the data shown); a strong line at 28°. We hypothesize that these two molecules crystallize in tapes (9° and 10°), that adjacent tapes pack in a staggered conformation as a result of their asymmetric scalloped edges (14°), and that these tapes are stepped (28°).
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