Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 138, Issue 14, Pages 4881-4889Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jacs.6b01120
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Funding
- New York University Materials Research Science and Engineering Center (MRSEC) program of the National Science Foundation [DMR-1420073]
- DARPA [W31P4Q1210008, W31P4Q1310005]
- Australian Research Council [FT130100463, DP140101776]
- EPSRC [EP/J01110X/1]
- NSF [CHE-0840277]
- Division Of Materials Research
- Direct For Mathematical & Physical Scien [1105000] Funding Source: National Science Foundation
- Division Of Mathematical Sciences
- Direct For Mathematical & Physical Scien [0931852] Funding Source: National Science Foundation
- Engineering and Physical Sciences Research Council [EP/J01110X/1] Funding Source: researchfish
- EPSRC [EP/J01110X/1] Funding Source: UKRI
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Structures of the alpha and beta phases of resorcinol, a major commodity chemical in the pharmaceutical, agrichemical, and polymer industries, were the first polymorphic pair of molecular crystals solved by X-ray analysis. It was recently stated that no additional phases can be found under atmospheric conditions (Druzbicki, K. et al. J. Phys. Chem. B 2015, 119, 1681). Herein is described the growth and structure of a new ambient pressure phase, epsilon, through a combination of optical and X-ray crystallography and by computational crystal structure prediction algorithms. alpha-Resorcinol has long been a model for mechanistic crystal growth studies from both solution and vapor because prisms extended along the polar axis grow much faster in one direction than in the opposite direction. Research has focused on identifying the absolute sense of the fast direction the so-called resorcinol riddle with the aim of identifying how solvent controls crystal growth. Here, the growth velocity dissymmetry in the melt is analyzed for the beta phase. The epsilon phase only grows from the melt, concomitant with the beta phase, as polycrystalline, radially growing spherulites. If the radii are polar, then the sense of the polar axis is an essential feature of the form. Here, this determination is made for spherulites of beta resorcinol (epsilon, point symmetry 222, does not have a polar axis) with additives that stereoselectively modify growth velocities. Both beta and epsilon have the additional feature that individual radial lamellae may adopt helicoidal morphologies. We correlate the appearance of twisting in beta and epsilon with the symmetry of twist-inducing additives.
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