Synthesis and retrostructural analysis of libraries of AB3 and constitutional isomeric AB2 phenylpropyl ether-based supramolecular dendrimers

Journal of the American Chemical Society
Virgil PercecPaul A Heiney

Abstract

We report the synthesis of methyl esters of 3-(4-hydroxyphenyl)propionic, 3-(3,4-dihydroxyphenyl)propionic, 3-(3,5-dihydroxyphenyl)propionic, and 3-(3,4,5-trihydroxyphenyl)propionic acids and their use in a convergent iterative strategy to prepare up to four generations of three libraries, one of 3,4,5- and two of constitutional isomeric 3,4- and 3,5-substituted 3-phenylpropyl dendrons. Each library contains 3-[3,4,5-tris(dodecyl-1-oxy)phenyl]propyl-, 3-[3,4-bis(dodecyl-1-oxy)phenyl]propyl-, 3-{3,4-bis[3-(4-dodecyl-1-oxyphenyl)propyl-1-oxy]phenyl}propyl-, and 3-{3,4,5-tris[3-(4-dodecyl-1-oxyphenyl)propyl-1-oxy]phenyl}propyl ether first-generation dendrons on their periphery and -CO2CH3, -COOH, and -CH2OH groups at their apex. Regardless of their generation number and their periphery, internal, and apex structures, these dendrons self-assemble into supramolecular dendrimers that self-organize into all periodic and quasi-periodic assemblies encountered previously and in several unencountered with architecturally related benzyl ether-based supramolecular dendrimers. A variety of porous columnar lattices that were previously obtained only from dendritic dipeptides and hollow supramolecular spheres were also discovered from these bu...Continue Reading

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Citations

May 27, 2011·Microbial Ecology·Federica VillaFrancesca Cappitelli
Jul 31, 2007·Chemical Society Reviews·Bertrand DonnioDaniel Guillon
Oct 6, 2010·Proceedings of the National Academy of Sciences of the United States of America·Pol BeseniusE W Meijer
Sep 16, 2006·Philosophical Transactions. Series A, Mathematical, Physical, and Engineering Sciences·Virgil Percec
Jan 1, 2010·Acta Crystallographica. Section E, Structure Reports Online·E SongH Reuter
Oct 16, 2010·Science·Mihai Peterca, Virgil Percec
Apr 10, 2010·Bioscience, Biotechnology, and Biochemistry·Keisuke TakahashiJun Kawabata
Mar 9, 2017·Proceedings of the National Academy of Sciences of the United States of America·Davit JishkarianiVirgil Percec
Oct 18, 2014·Chemical Society Reviews·Hao-Jan SunVirgil Percec
Jun 23, 2018·Soft Matter·Michael PfletscherMichael Giese
Jun 29, 2010·Chemistry : a European Journal·Yongguang LiVivian Wing-Wah Yam
Oct 18, 2006·Angewandte Chemie·Alessio PiermatteiDavid N Reinhoudt
Jan 17, 2007·Chemistry : a European Journal·Virgil PercecPaul A Heiney
Sep 26, 2007·Chemistry : a European Journal·Virgil PercecPaul A Heiney
Nov 21, 2007·Chemistry : a European Journal·Virgil PercecPaul A Heiney
Nov 1, 2009·Nature Chemistry·Yoshimitsu Sagara, Takashi Kato
Aug 18, 2010·Angewandte Chemie·Brad M RosenVirgil Percec
Jun 4, 2019·Dalton Transactions : an International Journal of Inorganic Chemistry·Soomin HyunOk-Sang Jung
Aug 13, 2013·Angewandte Chemie·Carsten Tschierske
Jan 22, 2020·Chemistry : a European Journal·Ruimeng ZhangStephen Z D Cheng
Feb 17, 2007·Chemistry : a European Journal·Virgil PercecPaul A Heiney
Oct 10, 2008·Journal of the American Chemical Society·Mihai PetercaPaul A Heiney
Mar 25, 2009·Journal of the American Chemical Society·Virgil PercecPaul A Heiney
Sep 6, 2008·Journal of the American Chemical Society·Virgil PercecPaul A Heiney
Jan 1, 2009·Journal of the American Chemical Society·Virgil PercecPaul A Heiney
Jul 30, 2010·Chemical Reviews·George R Newkome, Carol Shreiner
Aug 12, 2010·Journal of the American Chemical Society·Mihai PetercaVirgil Percec
Jun 28, 2011·Journal of the American Chemical Society·Virgil PercecSteven D Hudson
Dec 5, 2017·Journal of the American Chemical Society·Zhiwei LinStephen Z D Cheng
Jan 31, 2014·The Journal of Organic Chemistry·Irene R MárquezJuan M Cuerva

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