@article { ISI:000316451500010,
	title = {Easy and multigram-scale synthesis of pillar[5]quinone by the hypervalent iodine oxidation of 1,4-dimethoxypillar[5]arene},
	journal = {Synthesis-Stuttgart},
	volume = {45},
	number = {7},
	year = {2013},
	month = {APR},
	pages = {896-898},
	publisher = {GEORG THIEME VERLAG KG},
	address = {RUDIGERSTR 14, D-70469 STUTTGART, GERMANY},
	abstract = {<p>Pillar[5]quinone (P[5]Q), a potential molecule for anion recognition and supramolecular host-guest chemistry, has not as yet been used for practical purposes, presumably due to the synthetic difficulties in obtaining it in large amounts. Herein, we reveal an easy-to-operate and chromatography-free synthetic strategy that can furnish P[5]Q on a multigram scale; its success relies on the utility of hypervalent iodine, generated in situ from Oxone/ iodobenzene, as an efficient oxidant. Pillar[5]quinone was obtained in multigram quantities by oxidation of 1,4-dimethoxypillar[5]arene with Oxone/iodobenzene and simple purification by crystallization from 1,1,2,2-tetrachloroethane, thus opening up the opportunity to explore the properties of this interesting macrocyclic quinone.</p>},
	keywords = {hypervalent iodine oxidation, macromolecules, pillar-arenes, supramolecular chemistry},
	issn = {0039-7881},
	doi = {10.1055/s-0032-1318390},
	author = {Shivakumar, Kilingaru I. and Sanjayan, Gangadhar J.}
}
@article { ISI:000352246100007,
	title = {Exploiting powder x-ray diffraction to establish the solvent-assisted solid-state supramolecular assembly of pillar[5]quinone},
	journal = {Crystal Growth \& Design},
	volume = {15},
	number = {4},
	year = {2015},
	month = {APR},
	pages = {1583-1587},
	publisher = {AMER CHEMICAL SOC},
	address = {1155 16TH ST, NW, WASHINGTON, DC 20036 USA},
	abstract = {<p>We report the solvent-mediated supramolecular assembly of pillar[5]quinone (P[5]Q), a symmetric cyclamer containing five benzoquinone moieties bridged by five alternating methylene units. The supramolecular assembly of P[5]Q is shown to be facilitated by 1,1,2,2-tetrachloroethane (TCE) as solvent, producing a microcrystalline solvate material P[5]Q(.)2TCE with a fluffy texture. Optical and electron microscopy reveal that this material has a rod-shaped morphology, extending to several micrometers in length. Due to the microcrystalline nature of the material, structure determination was carried out directly from powder X-ray diffraction data, augmented by high-resolution solid-state C-13 NMR. The two crystallographically distinct TCE molecules occupy different types of void in the structure and have different dynamic properties. Crystallization of P[5]Q was attempted from a large number of different solvents, but only TCE was found to facilitate the formation of a crystalline phase. Indeed, features of the crystal structure suggest that the TCE component plays an important role in promoting the columnar assembly of P[5]Q molecules.</p>},
	issn = {1528-7483},
	doi = {10.1021/acs.cgd.5b00277},
	author = {Shivakumar, Kilingaru I. and Yan, Yuncheng and Hughes, Colan E. and Apperley, David C. and Harris, Kenneth D. M. and Sanjayan, Gangadhar J.}
}
