Janus faced fluorocyclohexanes for supramolecular assembly: synthesis and solid state structures of equatorial mono-, di- and tri alkylated cyclohexanes and with tri-axial C–F bonds to impart polarity

Thomas J. Poskin; Bruno A. Piscelli; Keigo Yoshida; David B. Cordes; Alexandra M. Z. Slawin; Rodrigo A. Cormanich; Shigeyuki Yamada; David O'Hagan

doi:10.1039/D2CC03010A

Janus faced fluorocyclohexanes for supramolecular assembly: synthesis and solid state structures of equatorial mono-, di- and tri alkylated cyclohexanes and with tri-axial C–F bonds to impart polarity

Thomas J. Poskin, Bruno A. Piscelli, Keigo Yoshida, David B. Cordes, Alexandra M. Z. Slawin, Rodrigo A. Cormanich, Shigeyuki Yamada, David O'Hagan^*

^*Corresponding author for this work

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

Abstract

Concise and general synthesis protocols are reported to generate all-syn mono-, di- and tri-alkylated cyclohexanes where a single fluorine is located on the remaining carbons of the ring. The alkyl groups are positioned to lie equatorially and to have triaxial C–F bonds imparting polarity to these ring systems. Intermolecular electrostatic interactions in the solid-state structure of the trialkylated systems are explored and the resultant supramolecular order opens up prospects for design in soft materials.

Original language	English
Pages (from-to)	7968-7971
Number of pages	4
Journal	Chemical Communications
Volume	58
Issue number	57
Early online date	20 Jun 2022
DOIs	https://doi.org/10.1039/D2CC03010A
Publication status	Published - 21 Jul 2022

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Poskin_2022_CC_Janus-faced-fluorocyclohexanes_CC
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CRITICAT - EASiCAT Studentship: CRITICAT - EASiCAT Studentship
Smith, A. D. (PI)
EPSRC
1/04/21 → 31/10/22
Project: Standard

CCDC 2174305 - 2174309: Experimental Crystal Structure Determination
Poskin, T. J. (Creator), Piscelli, B. A. (Creator), Yoshida, K. (Creator), Cordes, D. B. (Creator), Slawin, A. M. Z. (Creator), Cormanich, R. A. (Creator), Yamada, S. (Creator) & O'Hagan, D. (Creator), Cambridge Crystallographic Data Centre, 2022
DOI: 10.5517/ccdc.csd.cc2bzjwr, https://dx.doi.org/10.5517/ccdc.csd.cc2bzjxs and 3 more links, https://dx.doi.org/10.5517/ccdc.csd.cc2bzjyt, https://dx.doi.org/10.5517/ccdc.csd.cc2bzjzv, https://dx.doi.org/10.5517/ccdc.csd.cc2bzk0x (show fewer)
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Poskin, T. J., Piscelli, B. A., Yoshida, K., Cordes, D. B., Slawin, A. M. Z., Cormanich, R. A., Yamada, S., & O'Hagan, D. (2022). Janus faced fluorocyclohexanes for supramolecular assembly: synthesis and solid state structures of equatorial mono-, di- and tri alkylated cyclohexanes and with tri-axial C–F bonds to impart polarity. Chemical Communications, 58(57), 7968-7971. https://doi.org/10.1039/D2CC03010A

@article{57c31349615a4a6188de41484ada6150,

title = "Janus faced fluorocyclohexanes for supramolecular assembly: synthesis and solid state structures of equatorial mono-, di- and tri alkylated cyclohexanes and with tri-axial C–F bonds to impart polarity",

abstract = "Concise and general synthesis protocols are reported to generate all-syn mono-, di- and tri-alkylated cyclohexanes where a single fluorine is located on the remaining carbons of the ring. The alkyl groups are positioned to lie equatorially and to have triaxial C–F bonds imparting polarity to these ring systems. Intermolecular electrostatic interactions in the solid-state structure of the trialkylated systems are explored and the resultant supramolecular order opens up prospects for design in soft materials.",

author = "Poskin, {Thomas J.} and Piscelli, {Bruno A.} and Keigo Yoshida and Cordes, {David B.} and Slawin, {Alexandra M. Z.} and Cormanich, {Rodrigo A.} and Shigeyuki Yamada and David O'Hagan",

note = "We thank the EPSRC for a studentship (TJP) through the CRITICAT Doctoral Training Centre. FAPESP is also gratefully acknowledged for a studentship (BAP, #2021/09716-5) and a Young Researcher Award (RAC, #2018/03910-1).",

year = "2022",

month = jul,

day = "21",

doi = "10.1039/D2CC03010A",

language = "English",

volume = "58",

pages = "7968--7971",

journal = "Chemical Communications",

issn = "1359-7345",

publisher = "Royal Society of Chemistry",

number = "57",

}

Poskin, TJ, Piscelli, BA, Yoshida, K, Cordes, DB , Slawin, AMZ, Cormanich, RA, Yamada, S & O'Hagan, D 2022, 'Janus faced fluorocyclohexanes for supramolecular assembly: synthesis and solid state structures of equatorial mono-, di- and tri alkylated cyclohexanes and with tri-axial C–F bonds to impart polarity', Chemical Communications, vol. 58, no. 57, pp. 7968-7971. https://doi.org/10.1039/D2CC03010A

Janus faced fluorocyclohexanes for supramolecular assembly: synthesis and solid state structures of equatorial mono-, di- and tri alkylated cyclohexanes and with tri-axial C–F bonds to impart polarity. / Poskin, Thomas J.; Piscelli, Bruno A.; Yoshida, Keigo et al.
In: Chemical Communications, Vol. 58, No. 57, 21.07.2022, p. 7968-7971.

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

TY - JOUR

T1 - Janus faced fluorocyclohexanes for supramolecular assembly

T2 - synthesis and solid state structures of equatorial mono-, di- and tri alkylated cyclohexanes and with tri-axial C–F bonds to impart polarity

AU - Poskin, Thomas J.

AU - Piscelli, Bruno A.

AU - Yoshida, Keigo

AU - Cordes, David B.

AU - Slawin, Alexandra M. Z.

AU - Cormanich, Rodrigo A.

AU - Yamada, Shigeyuki

AU - O'Hagan, David

N1 - We thank the EPSRC for a studentship (TJP) through the CRITICAT Doctoral Training Centre. FAPESP is also gratefully acknowledged for a studentship (BAP, #2021/09716-5) and a Young Researcher Award (RAC, #2018/03910-1).

PY - 2022/7/21

Y1 - 2022/7/21

N2 - Concise and general synthesis protocols are reported to generate all-syn mono-, di- and tri-alkylated cyclohexanes where a single fluorine is located on the remaining carbons of the ring. The alkyl groups are positioned to lie equatorially and to have triaxial C–F bonds imparting polarity to these ring systems. Intermolecular electrostatic interactions in the solid-state structure of the trialkylated systems are explored and the resultant supramolecular order opens up prospects for design in soft materials.

AB - Concise and general synthesis protocols are reported to generate all-syn mono-, di- and tri-alkylated cyclohexanes where a single fluorine is located on the remaining carbons of the ring. The alkyl groups are positioned to lie equatorially and to have triaxial C–F bonds imparting polarity to these ring systems. Intermolecular electrostatic interactions in the solid-state structure of the trialkylated systems are explored and the resultant supramolecular order opens up prospects for design in soft materials.

U2 - 10.1039/D2CC03010A

DO - 10.1039/D2CC03010A

M3 - Article

SN - 1359-7345

VL - 58

SP - 7968

EP - 7971

JO - Chemical Communications

JF - Chemical Communications

IS - 57

ER -

Poskin TJ, Piscelli BA, Yoshida K, Cordes DB , Slawin AMZ, Cormanich RA et al. Janus faced fluorocyclohexanes for supramolecular assembly: synthesis and solid state structures of equatorial mono-, di- and tri alkylated cyclohexanes and with tri-axial C–F bonds to impart polarity. Chemical Communications. 2022 Jul 21;58(57):7968-7971. Epub 2022 Jun 20. doi: 10.1039/D2CC03010A

Janus faced fluorocyclohexanes for supramolecular assembly: synthesis and solid state structures of equatorial mono-, di- and tri alkylated cyclohexanes and with tri-axial C–F bonds to impart polarity

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Projects

CRITICAT - EASiCAT Studentship: CRITICAT - EASiCAT Studentship

Datasets

CCDC 2174305 - 2174309: Experimental Crystal Structure Determination

Cite this