Regiocontrol of the [2 + 2] Photodimerization in the Solid State Using Isosteric Resorcinols: Head-to-Tail Cyclobutane Formation via Unexpected Embraced Assemblies

Devin P. Ericson; Zachary P. Zurfluh-Cunningham; Ryan H. Groeneman; Elizabeth Elacqua; Eric W. Reinheimer; Bruce C. Noll; Leonard R. MacGillivray

doi:10.1021/acs.cgd.5b00939

Regiocontrol of the [2 + 2] Photodimerization in the Solid State Using Isosteric Resorcinols: Head-to-Tail Cyclobutane Formation via Unexpected Embraced Assemblies

Devin P. Ericson, Zachary P. Zurfluh-Cunningham, Ryan H. Groeneman, Elizabeth Elacqua, Eric W. Reinheimer, Bruce C. Noll, Leonard R. MacGillivray

Chemistry

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21 Scopus citations

Abstract

Regiocontrolled head-to-head and head-to-tail [2 + 2] photodimerizations of (E)-methyl-3-(pyridin-3-yl)prop-2-enoate are achieved in the solid state using 4,6-di-X-res (where X = Cl, Br, I; res = resorcinol) as small-molecule templates. The components in each co-crystal form discrete, three-component supramolecular assemblies sustained by two O-H···N hydrogen bonds. Whereas the head-to-head photoproduct (rctt)-dimethyl-3,4-bis(pyridin-3-yl)cyclobutane-1,2-dicarboxylate forms using 4,6-di-X-res (X = Cl or Br), the head-to-tail regioisomer (rctt)-dimethyl-2,4-bis(pyridin-3-yl)cyclobutane-1,3-dicarboxylate forms using 4,6-di-I-res. The head-to-tail product is generated via unexpected embraced dimeric assemblies. The stereochemistry of the head-to-tail product is confirmed using single-crystal X-ray diffraction.

Original language	English (US)
Pages (from-to)	5744-5748
Number of pages	5
Journal	Crystal Growth and Design
Volume	15
Issue number	12
DOIs	https://doi.org/10.1021/acs.cgd.5b00939
State	Published - Oct 21 2015

All Science Journal Classification (ASJC) codes

Chemistry(all)
Materials Science(all)
Condensed Matter Physics

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Ericson, D. P., Zurfluh-Cunningham, Z. P., Groeneman, R. H., Elacqua, E., Reinheimer, E. W., Noll, B. C., & MacGillivray, L. R. (2015). Regiocontrol of the [2 + 2] Photodimerization in the Solid State Using Isosteric Resorcinols: Head-to-Tail Cyclobutane Formation via Unexpected Embraced Assemblies. Crystal Growth and Design, 15(12), 5744-5748. https://doi.org/10.1021/acs.cgd.5b00939

Ericson, Devin P. ; Zurfluh-Cunningham, Zachary P. ; Groeneman, Ryan H. ; Elacqua, Elizabeth ; Reinheimer, Eric W. ; Noll, Bruce C. ; MacGillivray, Leonard R. / Regiocontrol of the [2 + 2] Photodimerization in the Solid State Using Isosteric Resorcinols : Head-to-Tail Cyclobutane Formation via Unexpected Embraced Assemblies. In: Crystal Growth and Design. 2015 ; Vol. 15, No. 12. pp. 5744-5748.

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title = "Regiocontrol of the [2 + 2] Photodimerization in the Solid State Using Isosteric Resorcinols: Head-to-Tail Cyclobutane Formation via Unexpected Embraced Assemblies",

abstract = "Regiocontrolled head-to-head and head-to-tail [2 + 2] photodimerizations of (E)-methyl-3-(pyridin-3-yl)prop-2-enoate are achieved in the solid state using 4,6-di-X-res (where X = Cl, Br, I; res = resorcinol) as small-molecule templates. The components in each co-crystal form discrete, three-component supramolecular assemblies sustained by two O-H···N hydrogen bonds. Whereas the head-to-head photoproduct (rctt)-dimethyl-3,4-bis(pyridin-3-yl)cyclobutane-1,2-dicarboxylate forms using 4,6-di-X-res (X = Cl or Br), the head-to-tail regioisomer (rctt)-dimethyl-2,4-bis(pyridin-3-yl)cyclobutane-1,3-dicarboxylate forms using 4,6-di-I-res. The head-to-tail product is generated via unexpected embraced dimeric assemblies. The stereochemistry of the head-to-tail product is confirmed using single-crystal X-ray diffraction.",

author = "Ericson, {Devin P.} and Zurfluh-Cunningham, {Zachary P.} and Groeneman, {Ryan H.} and Elizabeth Elacqua and Reinheimer, {Eric W.} and Noll, {Bruce C.} and MacGillivray, {Leonard R.}",

note = "Publisher Copyright: {\textcopyright} 2015 American Chemical Society.",

year = "2015",

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day = "21",

doi = "10.1021/acs.cgd.5b00939",

language = "English (US)",

volume = "15",

pages = "5744--5748",

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Ericson, DP, Zurfluh-Cunningham, ZP, Groeneman, RH, Elacqua, E, Reinheimer, EW, Noll, BC & MacGillivray, LR 2015, 'Regiocontrol of the [2 + 2] Photodimerization in the Solid State Using Isosteric Resorcinols: Head-to-Tail Cyclobutane Formation via Unexpected Embraced Assemblies', Crystal Growth and Design, vol. 15, no. 12, pp. 5744-5748. https://doi.org/10.1021/acs.cgd.5b00939

Regiocontrol of the [2 + 2] Photodimerization in the Solid State Using Isosteric Resorcinols : Head-to-Tail Cyclobutane Formation via Unexpected Embraced Assemblies. / Ericson, Devin P.; Zurfluh-Cunningham, Zachary P.; Groeneman, Ryan H.; Elacqua, Elizabeth; Reinheimer, Eric W.; Noll, Bruce C.; MacGillivray, Leonard R.

In: Crystal Growth and Design, Vol. 15, No. 12, 21.10.2015, p. 5744-5748.

Research output: Contribution to journal › Article › peer-review

TY - JOUR

T1 - Regiocontrol of the [2 + 2] Photodimerization in the Solid State Using Isosteric Resorcinols

T2 - Head-to-Tail Cyclobutane Formation via Unexpected Embraced Assemblies

AU - Ericson, Devin P.

AU - Zurfluh-Cunningham, Zachary P.

AU - Groeneman, Ryan H.

AU - Elacqua, Elizabeth

AU - Reinheimer, Eric W.

AU - Noll, Bruce C.

AU - MacGillivray, Leonard R.

PY - 2015/10/21

Y1 - 2015/10/21

N2 - Regiocontrolled head-to-head and head-to-tail [2 + 2] photodimerizations of (E)-methyl-3-(pyridin-3-yl)prop-2-enoate are achieved in the solid state using 4,6-di-X-res (where X = Cl, Br, I; res = resorcinol) as small-molecule templates. The components in each co-crystal form discrete, three-component supramolecular assemblies sustained by two O-H···N hydrogen bonds. Whereas the head-to-head photoproduct (rctt)-dimethyl-3,4-bis(pyridin-3-yl)cyclobutane-1,2-dicarboxylate forms using 4,6-di-X-res (X = Cl or Br), the head-to-tail regioisomer (rctt)-dimethyl-2,4-bis(pyridin-3-yl)cyclobutane-1,3-dicarboxylate forms using 4,6-di-I-res. The head-to-tail product is generated via unexpected embraced dimeric assemblies. The stereochemistry of the head-to-tail product is confirmed using single-crystal X-ray diffraction.

AB - Regiocontrolled head-to-head and head-to-tail [2 + 2] photodimerizations of (E)-methyl-3-(pyridin-3-yl)prop-2-enoate are achieved in the solid state using 4,6-di-X-res (where X = Cl, Br, I; res = resorcinol) as small-molecule templates. The components in each co-crystal form discrete, three-component supramolecular assemblies sustained by two O-H···N hydrogen bonds. Whereas the head-to-head photoproduct (rctt)-dimethyl-3,4-bis(pyridin-3-yl)cyclobutane-1,2-dicarboxylate forms using 4,6-di-X-res (X = Cl or Br), the head-to-tail regioisomer (rctt)-dimethyl-2,4-bis(pyridin-3-yl)cyclobutane-1,3-dicarboxylate forms using 4,6-di-I-res. The head-to-tail product is generated via unexpected embraced dimeric assemblies. The stereochemistry of the head-to-tail product is confirmed using single-crystal X-ray diffraction.

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DO - 10.1021/acs.cgd.5b00939

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JO - Crystal Growth and Design

JF - Crystal Growth and Design

SN - 1528-7483

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ER -

Regiocontrol of the [2 + 2] Photodimerization in the Solid State Using Isosteric Resorcinols: Head-to-Tail Cyclobutane Formation via Unexpected Embraced Assemblies

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