134881-72-4Relevant articles and documents
THE TEMPLATE-DIRECTED SYNTHESIS OF A ROTAXANE
Ashton, Peter R.,Grognuz, Michel,Slawin, Alexandra M. Z.,Stoddart, J. Frazer,Williams, David J.
, p. 6235 - 6238 (1991)
X-Ray crystallography, FABMS, and 1H and 13C NMR spectroscopy have all been employed in the characterization of a self-assembled rotaxane composed of (i) a polyether chain intercepted by a centrally-located ?-electron rich hydroquinol ring and terminat
Formation of huge cyclic oligomers in the condensation polymerization of bis(9-hydroxy-1,4,7-trioxanonyl) substituted naphthalene and benzenes with both aromatic and aliphatic bis-acid chlorides
Mertens, Ingrid J. A.,Wegh, Rene,Jenneskens, Leonardus W.,Vlietstra, Edward J.,Van Der Kerk-van Hoof, Anca,Zwikker, Jan W.,Cleij, Thomas J.,Smeets, Wilberth J. J.,Veldman, Nora,Spek, Anthony L.
, p. 725 - 736 (1998)
Without the use of high dilution techniques condensation polymerization of bis(9-hydroxy-1,4,7-trioxanonyl) substituted naphthalene and benzenes (1a-d) with the bis-acid chlorides terephthaloyl dichloride (2), adipoyl dichloride (5a) and isophthaloyl dich
Cu2+-induced blue shift of the pyrene excimer emission: A new signal transduction mode of pyrene probes
Yang, Jye-Shane,Lin, Che-Sheng,Hwang, Chung-Yu
, p. 889 - 892 (2001)
matrix presented A pentiptycene-bispyrenyl system (1) has been synthesized and investigated as a fluorescent chemosensor for metal ions. A novel blue shift along with an intensity enhancement of the pyrene excimer emission is observed for 1 in the presenc
Bistable [c2] Daisy Chain Rotaxanes as Reversible Muscle-like Actuators in Mechanically Active Gels
Goujon, Antoine,Lang, Thomas,Mariani, Giacomo,Moulin, Emilie,Fuks, Gad,Raya, Jesus,Buhler, Eric,Giuseppone, Nicolas
, p. 14825 - 14828 (2017)
The implementation of molecular machines in polymer science is of high interest to transfer mechanical motions from nanoscale to macroscale in order to access new kinds of active devices and materials. Toward this objective, thermodynamic and topological
One-Pot Synthesis of a Linear [4]Catenate Using Orthogonal Metal Templation and Ring-Closing Metathesis
Amir, Faheem,Barnes, Jonathan C.,Chang, Christy,Colley, Nathan D.,Fisher, Jeremy M.,Greene, Angelique F.,Li, Lei,Li, Ruihan,Li, Xuesong,Nosiglia, Mark A.
supporting information, (2020/08/12)
The efficient synthesis of well-defined, linear oligocatenanes possessing multiple mechanical bonds remains a formidable challenge in the field of mechanically interlocked molecules. Here, a one-pot synthetic strategy is described to prepare a linear [4]catenate using orthogonal metal templation between a macrocycle precursor, composed of terpyridine and phenanthroline ligands spaced by flexible glycol linkers, and a closed phenanthroline-based molecular ring. Implementation of two simultaneous ring-closing metathesis reactions after metal complexation resulted in the formation of three mechanical bonds. The linear [4]catenate product was isolated in 55% yield as a mixture of topological diastereomers. The intermediate metal complexes and corresponding interlocked products (with and without metals) were characterized by nuclear magnetic resonance, mass spectrometry, gel permeation chromatography, and UV-vis absorption spectroscopy. We envision that this general synthetic strategy may pave the way for the synthesis of higher order linear oligocatenates/catenanes with precise molecular weights and four or more interlocking molecular rings.
A new class of flavonoids bearing macrocyclic polyethers by stereoselective photochemical cycloaddition reaction
Ishikawa, Hiroki,Uemura, Naohiro,Taira, Ryo,Sano, Kento,Yoshida, Yasushi,Mino, Takashi,Kasashima, Yoshio,Sakamoto, Masami
, p. 3911 - 3916 (2019/06/18)
A new class of flavonoids bearing cyclic polyethers involving a phenyl ring was conveniently provided by the intramolecular photochemical dimerization of 2-chromonecarboxylic esters. Irradiation of 2-chromonecarboxylate with a polyether tethered at both ends promoted intramolecular [2 + 2] cyclobutane formation leading to 14- to 27-membered cyclic polyethers. The efficiency depended on the substituted position of the phenyl ring, with ortho- and meta-substituted derivatives giving cycloadducts in good chemical yields and quantum efficiencies, whereas the para-derivatives were inert toward photolysis. X-ray crystallographic analysis revealed that the stereochemistry of the macrocyclic cycloadducts exhibited C2-symmetry.
One-pot synthesis of cyclophane-type macrocycles using manganese(iii)- mediated oxidative radical cyclization
Ito, Yosuke,Tomiyasu, Yuichi,Kawanabe, Takahiro,Uemura, Keisuke,Ushimizu, Yuu,Nishino, Hiroshi
supporting information; scheme or table, p. 1491 - 1507 (2011/04/23)
Cyclophane-type macrocyclic compounds from 21 to 56 members having two fused dihydrofuran rings were synthesized by the manganese(iii)-mediated oxidation of terminal dienes with bis(3-oxobutanoate)s containing aromatics. The reaction detail, characterization and reaction pathways are described. The Royal Society of Chemistry 2011.
Synthesis of a mechanically linked oligo[2]rotaxane
Belaissaoui, Abdelhak,Shimada, Satoru,Ohishi, Akihiro,Tamaoki, Nobuyuki
, p. 2307 - 2310 (2007/10/03)
A bifunctional [2]rotaxane, bearing two free functional groups each in the ring and axial parts, was synthesized, followed by its polycondensation with methylene diphenyl diisocyanate leading to a mechanically linked oligo[2]rotaxane.
Molecular meccano. 1. [2]rotaxanes and a [2]catenane made to order
Anelli, Pier Lucio,Ashton, Peter R.,Ballardini, Roberto,Balzani, Vincenzo,Delgado, Milagros,Gandoffi, Maria Teresa,Goodnow, Timothy T.,Kaifer, Angel E.,Philp, Douglas,Pietraszkiewicz, Marek,Prodi, Luca,Reddington, Mark V.,Slawin, Alexandra M.Z.,Spencer, Neil,Fraser Stoddart,Vicent, Cristina,Williams, David J.
, p. 193 - 218 (2007/10/02)
A new synthetic strategy for the elaboration of supramolecular species and molecular compounds containing noncovalently interacting components is described, with the long-term objective of constructing highly ordered, wholly synthetic assemblies from readily available starting materials. These could serve as a basis for the future development of mechanoelectrical and photoelectrical communication systems and devices capable of storing and processing information. The approach was conceived against a background of a quarter of a century's experience in supramolecular, alias host-guest, chemistry. It is based on the use of irreversibly interlocked molecular systems that take the form of catenanes and rotaxanes. Such compounds are seen to be the ideal vehicles through which to transfer from supramolecular and host-guest chemistry the knowledge and experience gained from studying complexes between small chemical entities to very much larger molecular assemblies. Once we know how to interlock molecular components irreversibly and efficiently, we shall have a very much clearer idea on how to intertwine related polymer chains reversibly. A number of template-directed syntheses of [2]rotaxanes and a [2]catenane is discussed. They illustrate that there are inherently simple ways of making apparently complex unnatural products from appropriate substrates without the need for reagent control or catalysis. The noncovalent bonding interactions that are used to self-assemble the 1:1 complexes, which serve as precursors to the rotaxanes and the catenane, as well as to the [2]rotaxanes and the [2]catenane themselves, "live on" in their structures and superstructures after the self-assembly process is complete. A variety of methods, including X-ray crystallography, fast atom bombardment mass spectrometry, ultra violet-visible, luminescence, nuclear magnetic resonance, and electron spin resonance spectroscopies, and electrochemistry, demonstrate the high structural order that is incorporated into these new molecular assemblies in both the solid and solution states.
