TY - JOUR
T1 - Molecular Pedal Motion Influences Thermal Expansion Properties within Isostructural Hydrogen-Bonded Co-crystals
AU - Hutchins, Kristin M.
AU - Unruh, Daniel K.
AU - Verdu, Frank A.
AU - Groeneman, Ryan H.
N1 - Funding Information:
K.M.H gratefully acknowledges financial support from Texas Tech University in the form of startup funding. R.H.G. gratefully acknowledges financial support from Webster University in the form of various Faculty Research Grants.
Publisher Copyright:
© 2018 American Chemical Society.
PY - 2018/2/7
Y1 - 2018/2/7
N2 - The influence of molecular pedal motion on the thermal expansion properties of three isostructural hydrogen-bonded co-crystals based upon resorcinol is reported. The resulting co-crystals all exhibit discrete four-component assemblies held together by O-H···N hydrogen bonds and comprise resorcinol (res) with a series of isosteric bipyridines, namely, 4,4′-azopyridine (4,4′-AP), trans-1,2-bis(4-pyridyl)ethylene (4,4′-BPE), and 1,2-bis(4-pyridyl)acetylene (4,4′-BPA). The ability to change the core of the hydrogen bond acceptor molecules from an azo (N=N) to an ethylene (C=C) and finally an acetylene (C≡C) group affords co-crystals that differ in their tendency to undergo dynamic pedal motion in the organic solid state. All three co-crystals, 2(res)•2(4,4′-AP), 2(res) •2(4,4′-BPE), and 2(res) •2(4,4′-BPA), exhibit thermal expansions that correlate with the strength of the noncovalent interactions, as well as the propensity of the core to undergo pedal motion.
AB - The influence of molecular pedal motion on the thermal expansion properties of three isostructural hydrogen-bonded co-crystals based upon resorcinol is reported. The resulting co-crystals all exhibit discrete four-component assemblies held together by O-H···N hydrogen bonds and comprise resorcinol (res) with a series of isosteric bipyridines, namely, 4,4′-azopyridine (4,4′-AP), trans-1,2-bis(4-pyridyl)ethylene (4,4′-BPE), and 1,2-bis(4-pyridyl)acetylene (4,4′-BPA). The ability to change the core of the hydrogen bond acceptor molecules from an azo (N=N) to an ethylene (C=C) and finally an acetylene (C≡C) group affords co-crystals that differ in their tendency to undergo dynamic pedal motion in the organic solid state. All three co-crystals, 2(res)•2(4,4′-AP), 2(res) •2(4,4′-BPE), and 2(res) •2(4,4′-BPA), exhibit thermal expansions that correlate with the strength of the noncovalent interactions, as well as the propensity of the core to undergo pedal motion.
UR - http://www.scopus.com/inward/record.url?scp=85041903457&partnerID=8YFLogxK
U2 - 10.1021/acs.cgd.7b01386
DO - 10.1021/acs.cgd.7b01386
M3 - Article
AN - SCOPUS:85041903457
VL - 18
SP - 566
EP - 570
JO - Crystal Growth and Design
JF - Crystal Growth and Design
SN - 1528-7483
IS - 2
ER -