TY - JOUR
T1 - Unlocking pedal motion of the azo group
T2 - three- and unexpected eight-component hydrogen-bonded assemblies in co-crystals based on isosteric resorcinols
AU - Hutchins, Kristin M.
AU - Yelgaonkar, Shweta P.
AU - Harris-Conway, Brittany L.
AU - Reinheimer, Eric W.
AU - MacGillivray, Leonard R.
AU - Groeneman, Ryan H.
N1 - Publisher Copyright:
© 2018 Informa UK Limited, trading as Taylor & Francis Group.
Copyright:
Copyright 2018 Elsevier B.V., All rights reserved.
PY - 2018/6/3
Y1 - 2018/6/3
N2 - Co-crystallization of 3-phenylazopyridine (3PAzP) with dihalogenated resorcinols (res) 4,6-diX res (where: X = Cl, Br, and I) yields co-crystals that support molecular pedal motion in the crystalline state. The co-crystals are sustained by hydrogen-bonded assemblies, with the pattern of hydrogen-bonding drastically different based on the res. For 4,6-diCl res, an unexpected eight-component hydrogen-bonded assembly is realized, while three-component hydrogen-bonded assemblies are observed for 4,6-diBr res and 4,6-diI res. We show the co-crystallization approach to afford pedal motion in the azo core, while no such motion is present in the absence of a res. Pure 3PAzP packs to form a noncentrosymmetric herringbone structure.
AB - Co-crystallization of 3-phenylazopyridine (3PAzP) with dihalogenated resorcinols (res) 4,6-diX res (where: X = Cl, Br, and I) yields co-crystals that support molecular pedal motion in the crystalline state. The co-crystals are sustained by hydrogen-bonded assemblies, with the pattern of hydrogen-bonding drastically different based on the res. For 4,6-diCl res, an unexpected eight-component hydrogen-bonded assembly is realized, while three-component hydrogen-bonded assemblies are observed for 4,6-diBr res and 4,6-diI res. We show the co-crystallization approach to afford pedal motion in the azo core, while no such motion is present in the absence of a res. Pure 3PAzP packs to form a noncentrosymmetric herringbone structure.
KW - Crystal engineering
KW - azo compound
KW - co-crystal
KW - hydrogen bonding
KW - pedal motion
UR - http://www.scopus.com/inward/record.url?scp=85042216875&partnerID=8YFLogxK
U2 - 10.1080/10610278.2018.1435884
DO - 10.1080/10610278.2018.1435884
M3 - Article
AN - SCOPUS:85042216875
VL - 30
SP - 533
EP - 539
JO - Supramolecular Chemistry
JF - Supramolecular Chemistry
SN - 1061-0278
IS - 5-6
ER -