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Differential scanning calorimetry and powder XRD analyses revealed that all\u2010<jats:italic>trans<\/jats:italic> <jats:bold>L<\/jats:bold> and <jats:italic>gauche<\/jats:italic>\u2010rich <jats:bold>S<\/jats:bold> polymorphic forms appeared for the analogues with more than eight carbon atoms in the alkyl chain, that is, the polymorphism originates in the conformation of the alkyl groups and hydrogen\u2010bonding patterns of the benzamide group. Also, the trifluoromethyl substituent is crucial in that it provides an appropriate molecular balance between the benzamide and alkyl groups. Scanning electron microscopy and powder XRD analyses of solids obtained by a drying\u2010mediated assembly process revealed that production of the <jats:bold>L<\/jats:bold> polymorph by polymorphic transition from the <jats:bold>S<\/jats:bold> polymorph resulted in evolution of a three\u2010dimensional structure when the alkyl group has more than 12 carbon atoms. Among the series of compounds, <jats:bold>12FH2<\/jats:bold> and 4\u2010tetradecyloxy\u20102\u2010trifluoromethylbenzamide (<jats:bold>14FH2<\/jats:bold>) formed parallelogrammatic pipes with micrometer dimensions. An atomic force microscopy study of <jats:bold>12FH2<\/jats:bold> suggested that a single pipe may be composed of platelike crystallites of <jats:bold>L<\/jats:bold> polymorph. From a mercury\u2010intrusion porosimetry study, it was determined that macroporous materials with average pore diameters of about 40\u2005\u03bcm and porosity of about 80\u2009% were obtained. The previously proposed self\u2010templation mechanism by polymorphic transition from <jats:bold>S<\/jats:bold> to <jats:bold>L<\/jats:bold> polymorph was further discussed in view of polymorphism and the crystallization rate. An appropriate molecular balance between the benzamide and alkyl groups is necessary to induce a proper polymorphic transition for the development of a three\u2010dimensional hollow structure in the evaporation process.<\/jats:p>","DOI":"10.1002\/chem.200801408","type":"journal-article","created":{"date-parts":[[2008,12,9]],"date-time":"2008-12-09T18:09:30Z","timestamp":1228846170000},"page":"612-622","source":"Crossref","is-referenced-by-count":10,"title":["Utilization of Evaporation during the Crystallization Process: Self\u2010Templation of Organic Parallelogrammatic 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