Heteroditopic Calix[6]arene Based Intervowen and Interlocked Molecular Devices.
(Pseudo)rotaxanes
Calix[6]arenes
Catenanes
Mechanical Interlocked Molecules
Molecular Machines
Journal
Chemical record (New York, N.Y.)
ISSN: 1528-0691
Titre abrégé: Chem Rec
Pays: United States
ID NLM: 101085550
Informations de publication
Date de publication:
May 2021
May 2021
Historique:
revised:
17
02
2021
received:
18
01
2021
pubmed:
4
3
2021
medline:
4
3
2021
entrez:
3
3
2021
Statut:
ppublish
Résumé
Since the dawn of supramolecular chemistry, calixarenes have been employed as platforms onto which functional groups and binding sites can be loaded in a regio- and stereocontrolled manner for the recognition of charged and neutral species. Despite their wider annulus, potentially suitable to bind larger guests, the larger members of the calixarene series have been relatively less employed, mainly because of the synthetic difficulties to control their conformational flexibility and their regioselective functionalization. In this account, we will present the achievements gained during the last two decades on the use of the calix[6]arene as a platform to build-up structures in which the macrocycle acts as a wheel for the synthesis of oriented (pseudo)rotaxanes. We also account on how these calix[6]arene hosts affect the reactivity or spectroscopic properties of their bound guests.
Identifiants
pubmed: 33656250
doi: 10.1002/tcr.202100012
doi:
Types de publication
Journal Article
Review
Langues
eng
Sous-ensembles de citation
IM
Pagination
1161-1181Subventions
Organisme : Italian Ministry of University and Research
ID : PRIN 20173L7W8K
Organisme : Italian Ministry of University and Research
ID : FARE R16S9XXKX3
Informations de copyright
© 2021 The Authors. Published by The Chemical Society of Japan & Wiley-VCH GmbH.
Références
Supramolecular Chemistry, 8 Volume Set: From Molecules to Nanomaterials; J. W. Steed, P. A. Gale, Eds.; John Wiley & Sons, Ltd. 2012.
A. Credi, S. Silvi, M. Venturi, W. R. Browne, Molecular Machines and Motors: Recent Advances and Perspectives; A. Credi, S. Silvi, M. Venturi, Eds.; Topics in Current Chemistry Vol. 354; Springer International Publishing: Cham, 2014; Vol. 354.
C. J. Bruns, J. F. Stoddart, The Nature of the Mechanical Bond: From Molecules to Machines; John Wiley & Sons, Inc.: Hoboken, 2016.
J.-P. Sauvage, C. Dietrich-Buchecker, Molecular Catenanes, Rotaxanes and Knots: A Journey Through the World of Molecular Topology; J.-P. Sauvage, C. Dietrich-Buchecker, Eds.; Wiley-VCH Verlag GmbH: Weinhein, 2007.
J.-P. Sauvage, Angew. Chem. Int. Ed. 2017, 56, 11080-11093;
Angew. Chem. 2017, 129, 11228-11242.
Topology in Chemistry: Discrete Mathematics of Molecules; D. H. Rouvray, R. B. King, Eds.; Horwood Publishing Limited: Chichester, 2002.
J. W. Steed, D. R. Turner, K. J. Wallace, Core Concepts in Supramolecular Chemistry and Nanochemistry; John Wiley & Sons, Ltd: Chichester, 2007.
V. Balzani, M. Venturi, A. Credi, Molecular Devices and Machines - A Journey into the Nanoworld; Wiley-VCH Verlag GmbH: Weinheim 2003.
V. Balzani, A. Credi, M. Venturi, Molecular Devices and Machines: Concepts and Perspectives for the Nanoworld: Second Edition; Wiley-VCH Verlag GmbH: Weinheim, 2008.
M. Xue, Y. Yang, X. Chi, X. Yan, F. Huang, Chem. Rev. 2015, 115, 7398-7501.
C. Fischer, M. Nieger, O. Mogck, V. Böhmer, R. Ungaro, F. Vögtle, Eur. J. Org. Chem. 1998, 1998, 155-161.
M. Chas, P. Ballester, Chem. Sci. 2011, 3, 186-191.
C. Gaeta, M. O. Vysotsky, A. Bogdan, V. Böhmer, J. Am. Chem. Soc. 2005, 127, 13136-13137.
O. Molokanova, G. Podoprygorina, M. Bolte, V. Böhmer, Tetrahedron 2009, 65, 7220-7233.
M. Janke, Y. Rudzevich, O. Molokanova, T. Metzroth, I. Mey, G. Diezemann, P. E. Marszalek, J. Gauss, V. Böhmer, A. Janshoff, Nat. Nanotechnol. 2009, 4, 225-229.
A. Arduini, L. Domiano, L. Ogliosi, A. Pochini, A. Secchi, R. Ungaro, J. Org. Chem. 1997, 62, 7866-7868.
A. Arduini, R. Ferdani, A. Pochini, A. Secchi, F. Ugozzoli, G. M. Sheldrick, P. Prados, J. J. González, J. de Mendoza, J. Supramol. Chem. 2002, 2, 85-88.
J. J. González, R. Ferdani, E. Albertini, J. M. Blasco, A. Arduini, A. Pochini, P. Prados, J. de Mendoza, Chem. Eur. J. 2000, 6, 73-80.
A. Arduini, R. Ferdani, A. Pochini, A. Secchi, F. Ugozzoli, Angew. Chem. Int. Ed. 2000, 39, 3453-3456;
Angew. Chem. 2000, 112, 3595-3598.
A. Credi, S. Dumas, S. Silvi, M. Venturi, A. Arduini, A. Pochini, A. Secchi, J. Org. Chem. 2004, 69, 5881-5887.
A. Arduini, F. Calzavacca, A. Pochini, A. Secchi, Chem. Eur. J. 2003, 9, 793-799.
A. Arduini, F. Ciesa, M. Fragassi, A. Pochini, A. Secchi, Angew. Chem. Int. Ed. 2005, 44, 278-281;
Angew. Chem. 2005, 117, 282-285.
A. Arduini, R. Bussolati, A. Credi, G. Faimani, S. Garaudée, A. Pochini, A. Secchi, M. Semeraro, S. Silvi, M. Venturi, Chem. Eur. J. 2009, 15, 3230-3242.
A. Arduini, R. Bussolati, A. Credi, A. Secchi, S. Silvi, M. Semeraro, M. Venturi, J. Am. Chem. Soc. 2013, 135, 9924-9930.
J. D. Crowley, S. M. Goldup, A.-L. Lee, D. A. Leigh, R. T. McBurney, Chem. Soc. Rev. 2009, 38, 1530-1541.
G. Orlandini, G. Ragazzon, V. Zanichelli, A. Secchi, S. Silvi, M. Venturi, A. Arduini, A. Credi, Chem. Commun. 2017, 53, 6172-6174.
Partial redistribution of pseudorotaxane isomers P′/P“[2⊃7 a]OTs could be observed in toluene-d8 after refluxing at 373 K for several hours.
V. Zanichelli, G. Ragazzon, G. Orlandini, M. Venturi, A. Credi, S. Silvi, A. Arduini, A. Secchi, Org. Biomol. Chem. 2017, 15, 6753-6763.
G. Orlandini, V. Zanichelli, A. Secchi, A. Arduini, G. Ragazzon, A. Credi, M. Venturi, S. Silvi, Supramol. Chem. 2016, 28, 427-435.
A. Arduini, R. Bussolati, A. Credi, S. Monaco, A. Secchi, S. Silvi, M. Venturi, Chem. Eur. J. 2012, 18, 16203-16213.
A. Arduini, R. Bussolati, A. Credi, A. Pochini, A. Secchi, S. Silvi, M. Venturi, Tetrahedron 2008, 64, 8279-8286.
V. Zanichelli, G. Ragazzon, A. Arduini, A. Credi, P. Franchi, G. Orlandini, M. Venturi, M. Lucarini, A. Secchi, S. Silvi, Eur. J. Org. Chem. 2016, 2016, 1033-1042.
V. Zanichelli, M. Bazzoni, A. Arduini, P. Franchi, M. Lucarini, G. Ragazzon, A. Secchi, S. Silvi, Chem. Eur. J. 2018, 24, 12370-12382.
G. Orlandini, L. Casimiro, M. Bazzoni, B. Cogliati, A. Credi, M. Lucarini, S. Silvi, A. Arduini, A. Secchi, Org. Chem. Front. 2020, 7, 648-659.
V. Zanichelli, L. Dallacasagrande, A. Arduini, A. Secchi, G. Ragazzon, S. Silvi, A. Credi, Molecules 2018, 23, 1156-1168.
S. Silvi, A. Arduini, A. Pochini, A. Secchi, M. Tomasulo, F. M. Raymo, M. Baroncini, A. Credi, J. Am. Chem. Soc. 2007, 129, 13378-13379.
M. Bazzoni, F. Terenziani, A. Secchi, G. Cera, I. Jabin, G. De Leener, M. Luhmer, A. Arduini, Chem. Eur. J. 2020, 26, 3022-3025.
G. Cera, F. Cester Bonati, M. Bazzoni, A. Secchi, A. Arduini, Org. Biomol. Chem. 2021, 19, 1546-1554.
G. Cera, D. Balestri, M. Bazzoni, L. Marchiò, A. Secchi, A. Arduini, Org. Biomol. Chem. 2020, 18, 6241-6246.
G. Cera, M. Bazzoni, A. Arduini, A. Secchi, Org. Lett. 2020, 22, 3702-3705.
V. Iuliano, C. Talotta, C. Gaeta, N. Hickey, S. Geremia, I. Vatsouro, V. Kovalev, P. Neri, J. Org. Chem. 2020, 85, 12585-12593.
M. Tranfić Bakić, V. Iuliano, C. Talotta, S. Geremia, N. Hickey, A. Spinella, M. De Rosa, A. Soriente, C. Gaeta, P. Neri, J. Org. Chem. 2019, 84, 11922-11927.
S. Moerkerke, V. Malytskyi, L. Marcélis, J. Woutersc, I. Jabin, Org. Biomol. Chem. 2017, 15, 8967-8974.
C. Talotta, N. A. De Simone, C. Gaeta, P. Neri, Org. Lett. 2015, 17, 4, 1006-1009.
C. Gaeta, C. Talotta, P. Neri, Chem. Commun. 2014, 50, 9917-9920.
C. Talotta, C. Gaeta, Z. Qi, C. A. Schalley, P. Neri, Angew. Chem. Int. Ed. 2013, 52, 7437-7441;
Angew. Chem. 2013, 125, 7585-7589.
R. Ciao, C. Talotta, C. Gaeta, L. Margarucci, A. Casapullo, P. Neri, Org. Lett. 2013, 15, 5694-5697.
T. Pierro, C. Gaeta, C. Talotta, A. Casapullo, P. Neri, Org. Lett. 2011, 13, 2650-2653.
C. Gaeta, F. Troisi, P. Neri, Org. Lett. 2010, 12, 2092-2095.
M. Vlatković, B. S. L. Collins, B. L. Feringa, Chem. Eur. J. 2016, 22, 17080-17111.