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Structure and morphology of light-reflecting synthetic and biogenic polymorphs of isoxanthopterin: A comparison

Hirsch, Anna, Palmer, Benjamin A., Ramasubramaniam, Ashwin, Williams, P. Andrew, Harris, Kenneth D. M. ORCID:, Pokroy, Boaz, Weiner, Steve, Addadi, Lia, Leiserowitz, Leslie and Kronik, Leeor 2019. Structure and morphology of light-reflecting synthetic and biogenic polymorphs of isoxanthopterin: A comparison. Chemistry of Materials 31 (12) , pp. 4479-4489. 10.1021/acs.chemmater.9b01039

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Until recently it was thought that the only optical function of pteridines in biology was to act as light-absorbing pigments, but a recent report by some of us revealed that crystalline isoxanthopterin is a reflector in the eyes of decapod crustaceans. Here, we report the formation of crystalline isoxanthopterin synthetically from the polar dimethyl sulfoxide solvent, with X-ray diffraction analysis revealing a crystal structure different from that of biogenic isoxanthopterin. The structure of the new polymorph was determined in two independent ways. In one approach, it was generated and optimized using first-principles calculations, followed by comparison of simulation and experiment for high-resolution powder X-ray diffraction (PXRD) and electron diffraction. In the other approach, the structure was obtained definitively from PXRD data using a direct-space genetic algorithm for structure solution followed by Rietveld refinement. The synthetic structure is different from its biogenic counterpart, especially in having a nonplanar criss-cross H-bonded arrangement. We also rationalized the morphology of the crystals and the effect of the DMSO thereon, via a comparison between observed and theoretical growth morphologies. In addition, we calculated the optical properties of the synthetic structure and found its two dominant refractive indices to be somewhat lower than those of its biogenic counterpart, but still as high as those of reflecting guanine crystals. Synthetic isoxanthopterin therefore emerges as a promising candidate for incorporation in artificial optical systems.

Item Type: Article
Date Type: Publication
Status: Published
Schools: Chemistry
Publisher: American Chemical Society
ISSN: 0897-4756
Date of First Compliant Deposit: 20 June 2019
Date of Acceptance: 30 May 2019
Last Modified: 07 Nov 2023 10:37

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