Investigations into the assembly behaviour of a ‘rigidified’ p -carboxylatocalix[4]arene

Fairbairn, Robyn E.; Teat, Simon J.; Ling, Irene; Dalgarno, Scott J.

doi:10.1039/c9ce01326a

Title: Investigations into the assembly behaviour of a ‘rigidified’ p -carboxylatocalix[4]arene

Journal Article · Thu Oct 17 00:00:00 EDT 2019 · CrystEngComm

DOI:https://doi.org/10.1039/c9ce01326a· OSTI ID:1581760

Fairbairn, Robyn E. ^[1];

^[2];

^[3];

^[1]

Heriot-Watt Univ., Edinburgh (United Kingdom)
Lawrence Berkeley National Lab. (LBNL), Berkeley, CA (United States)
Monash Univ. Malaysia, Selangor (Malaysia)

The p-carboxylatocalix[4]arenes have been shown to be versatile supramolecular building blocks capable of forming a range of bi-layers, capsules and nanoscale tubules in the solid state. In this work, we report the synthesis of a new ‘rigidified’ analogue, as well as investigations into its self-assembly and related coordination chemistry. These behaviours are reminiscent of other p-carboxylatocalix[4]arenes despite the presence of rigidifying groups at the lower-rim, suggesting that this building block may be further exploited in the assembly of a range of new metal–organic cages and coordination polymers.

View Accepted Manuscript (DOE)

Cite

Export

Save

Research Organization:: Lawrence Berkeley National Lab. (LBNL), Berkeley, CA (United States)

Sponsoring Organization:: USDOE Office of Science (SC), Basic Energy Sciences (BES); Royal Society Newton Mobility Fund

Grant/Contract Number:: AC02-05CH11231; NI170151

OSTI ID:: 1581760

Journal Information:: CrystEngComm, Vol. 21, Issue 43; ISSN 1466-8033

Publisher:: Royal Society of ChemistryCopyright Statement

Country of Publication:: United States

Language:: English

Citation Metrics:

Cited by: 1 work

Citation information provided by
Web of Science

References (26)

Recent Topics on Functionalization and Recognition Ability of Calixarenes: The ‘Third Host Molecule’ Takeshita, Michinori; Shinkai, Seiji Bulletin of the Chemical Society of Japan, Vol. 68, Issue 4 https://doi.org/10.1246/bcsj.68.1088	journal	April 1995
Inherently chiral α-picolyloxy-p-tert-butylcalix[5]arene crown ethers: Synthesis, structure proof, and enantioselective HPLC resolution Caccamese, Salvatore; Notti, Anna; Pappalardo, Sebastiano Tetrahedron, Vol. 55, Issue 17 https://doi.org/10.1016/S0040-4020(99)00195-7	journal	April 1999
Selective 1,2-functionalization of calix[4]arenes at the lower rim. Synthesis of a new type of bis-calixcrown ether Arduini, Arturo; Casnati, Alessandro; Dodi, Lorenzo Journal of the Chemical Society, Chemical Communications, Issue 22 https://doi.org/10.1039/c39900001597	journal	January 1990
Salt formation affects the conformational and assembly properties of p-carboxylatocalix[4]arenes Kennedy, Stuart; Beavers, Christine M.; Teat, Simon J. CrystEngComm, Vol. 16, Issue 18 https://doi.org/10.1039/C3CE42523A	journal	January 2014
Synthesis and Evaluation of Novel ¹⁸ F Labeled 2-Pyridinylbenzoxazole and 2-Pyridinylbenzothiazole Derivatives as Ligands for Positron Emission Tomography (PET) Imaging of β-Amyloid Plaques Cui, Mengchao; Wang, Xuedan; Yu, Pingrong Journal of Medicinal Chemistry, Vol. 55, Issue 21 https://doi.org/10.1021/jm300973k	journal	September 2012
Recurrence of Carboxylic Acid−Pyridine Supramolecular Synthon in the Crystal Structures of Some Pyrazinecarboxylic Acids Vishweshwar, Peddy; Nangia, Ashwini; Lynch, Vincent M. The Journal of Organic Chemistry, Vol. 67, Issue 2 https://doi.org/10.1021/jo0162484	journal	January 2002
Calix[4]arenes Blocked in a Rigid Cone Conformation by Selective Functionalization at the Lower Rim Arduini, Arturo; Fabbi, Massimo; Mantovani, Marco The Journal of Organic Chemistry, Vol. 60, Issue 5 https://doi.org/10.1021/jo00110a055	journal	March 1995
Pyridine Directed Assembly of Tetra- O -Alkyl p -Carboxylatocalix[4]arenes Kennedy, Stuart; Beavers, Christine M.; Teat, Simon J. Crystal Growth & Design, Vol. 12, Issue 2 https://doi.org/10.1021/cg2008864	journal	January 2012
Design and synthesis of multiple-loop receptors based on a calix〚4〛arene scaffold for protein surface recognition Lin, Qing; Hamilton, Andrew D. Comptes Rendus Chimie, Vol. 5, Issue 5 https://doi.org/10.1016/S1631-0748(02)01408-X	journal	May 2002
Metal–organic calixarene capsules: the evolution of controlled assembly Cholewa, Piotr P.; Dalgarno, Scott J. CrystEngComm, Vol. 16, Issue 18 https://doi.org/10.1039/c3ce42169d	journal	January 2014
Directed assembly via selectively positioned host functionality Cholewa, Piotr P.; Beavers, Christine M.; Teat, Simon J. Chemical Communications, Vol. 49, Issue 31 https://doi.org/10.1039/c3cc40564h	journal	January 2013
Synthesis of selectively formylated calixarene ethers Arora, Vandna; Chawla, H. M.; Santra, Anuradha Tetrahedron, Vol. 58, Issue 28 https://doi.org/10.1016/S0040-4020(02)00551-3	journal	July 2002
Pyridine Directed Assembly of Di- O -Alkyl-tris- p -Carboxylatocalix[4]arenes Kennedy, Stuart; Dodgson, India E.; Beavers, Christine M. Crystal Growth & Design, Vol. 12, Issue 2 https://doi.org/10.1021/cg200887d	journal	January 2012
Modulation of nanotube packing through the controlled self-assembly of tris-p-carboxylatocalix[4]arenes Kennedy, Stuart; Dalgarno, Scott J. Chemical Communications, Issue 35 https://doi.org/10.1039/b909456c	journal	January 2009
New opportunities in synthetic macrocyclic arenes Wu, Jia-Rui; Yang, Ying-Wei Chemical Communications, Vol. 55, Issue 11 https://doi.org/10.1039/C8CC09374A	journal	January 2019
Eliminating disorder in a self-assembled calixarene nanotube Kennedy, Stuart; Cholewa, Piotr; McIntosh, Ruaraidh D. CrystEngComm, Vol. 15, Issue 8 https://doi.org/10.1039/C2CE26536B	journal	January 2013
Enhancing Strategies for the Assembly of Metal–Organic Systems with Inherent Cavity-Containing Calix[4]arenes Cholewa, Piotr P.; Beavers, Christine M.; Teat, Simon J. Crystal Growth & Design, Vol. 13, Issue 12 https://doi.org/10.1021/cg4013685	journal	November 2013
Calixarenes, Macrocycles with (Almost) Unlimited Possibilities Böhmer, Volker Angewandte Chemie International Edition in English, Vol. 34, Issue 7, p. 713-745 https://doi.org/10.1002/anie.199507131	journal	April 1995
Synthesis of 1,2-bridged calix[4]arene-biscrowns in the 1,2-alternate conformation Arduini, Arturo; Domiano, Laura; Pochini, Andrea Tetrahedron, Vol. 53, Issue 10 https://doi.org/10.1016/S0040-4020(97)00097-5	journal	March 1997
Rigid cone calix[4]arenes as π-donor systems: complexation of organic molecules and ammonium ions in organic media Arduini, Arturo; McGregor, William M.; Paganuzzi, Daniela J. Chem. Soc., Perkin Trans. 2, Issue 5 https://doi.org/10.1039/P29960000839	journal	January 1996
Synthesis, and X-ray crystal and molecular structure of a novel macro-bicyclic ligand: crowned p-t-butyl-calix[4]arene Alfieri, Carla; Dradi, Emanuele; Pochini, Andrea Journal of the Chemical Society, Chemical Communications, Issue 19 https://doi.org/10.1039/c39830001075	journal	January 1983
Calixarenenanotubes: structural tolerance towards pyridine templates Kennedy, Stuart; Beavers, Christine M.; Teat, Simon J. New J. Chem., Vol. 35, Issue 1 https://doi.org/10.1039/C0NJ00605J	journal	January 2011
Guest Transport in a Nonporous Organic Solid via Dynamic van der Waals Cooperativity Atwood, J. L.; Barbour, L. J.; Jerga, A. Science, Vol. 298, Issue 5595 https://doi.org/10.1126/science.1077591	journal	November 2002
Metal-Organic Calixarene Nanotubes Kennedy, Stuart; Karotsis, Georgios; Beavers, Christine M. Angewandte Chemie International Edition, Vol. 49, Issue 25 https://doi.org/10.1002/anie.201001078	journal	May 2010
Versatile assembly of p-carboxylatocalix[4]arene-O-alkyl ethers Kennedy, Stuart; Teat, Simon J.; Dalgarno, Scott J. Dalton Trans., Vol. 39, Issue 2 https://doi.org/10.1039/B914133B	journal	January 2010
Metal-Organic Calixarene Nanotubes Kennedy, Stuart; Karotsis, Georgios; Beavers, Christine M. Angewandte Chemie, Vol. 122, Issue 25 https://doi.org/10.1002/ange.201001078	journal	May 2010

Linked Research (4)

Figures / Tables (8)

Similar Records

A Convenient Synthetic Route to Partial-Cone p-Carboxylatocalix[4]arenes

Journal Article · Wed Sep 30 00:00:00 EDT 2015 · Chimia · OSTI ID:1581760

Fairbairn, Robyn E.; Teat, Simon J.; Gagnon, Kevin J.; +1 more

Versatile assembly of p-carboxylatocalix[4]arene-O-alkyl ethers

Journal Article · Wed Jul 08 00:00:00 EDT 2009 · Dalton Transactions · OSTI ID:1581760

Kennedy, Stuart; Teat, Simon J; Dalgarno, Scott J

Calix[4]arene Based Single-Molecule Magnets

Journal Article · Thu Jun 04 00:00:00 EDT 2009 · Angewandte Chemie · OSTI ID:1581760

Karotsis, Georgios; Teat, Simon J; Wernsdorfer, Wolfgang; +3 more

Related Subjects

37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY

CCDC 1948423: Experimental Crystal Structure Determination E., Fairbairn, Robyn; J., Teat, Simon; Irene, Ling, https://doi.org/10.5517/ccdc.csd.cc23dhcd The current record is supplemented by this dataset	dataset	January 2019
CCDC 1948424: Experimental Crystal Structure Determination E., Fairbairn, Robyn; J., Teat, Simon; Irene, Ling, https://doi.org/10.5517/ccdc.csd.cc23dhdf The current record is supplemented by this dataset	dataset	January 2019
CCDC 1948425: Experimental Crystal Structure Determination E., Fairbairn, Robyn; J., Teat, Simon; Irene, Ling, https://doi.org/10.5517/ccdc.csd.cc23dhfg The current record is supplemented by this dataset	dataset	January 2019
CCDC 1948426: Experimental Crystal Structure Determination E., Fairbairn, Robyn; J., Teat, Simon; Irene, Ling, https://doi.org/10.5517/ccdc.csd.cc23dhgh The current record is supplemented by this dataset	dataset	January 2019