β-Cyclodextrin Supramolecular Recognition of bis-Cationic Dithienylethenes
Giulio Bianchini, Mattia Bazan, Fabrizio Fabris, Alessandro Scarso
Organics · pp. 77–86 · Published 6 Apr 2022
10.3390/org3020005Abstract
The supramolecular interactions in water between β-cyclodextrin and the open and closed photochromic forms of two bis-cationic dithienylethenes, characterized by different electronic properties, were investigated aiming at underlying the key aspects of the recognition process. The dithienylethene equipped with the cyclopentenyl unit showed a difference in binding free energies to the β-cyclodextrin between the open and closed photochromic forms of about 1 kJ/mol. Conversely, the dithienylethene equipped with the perfluorinated cyclopentenyl unit not only was a better guest but showed a three times higher difference in the binding of free energies between the open and closed isomers.
References (49)
- 1 Neilson, 2012, Photoswitchable Organocatalysis: Using Light To Modulate the Catalytic Activities of N-Heterocyclic Carbenes [DOI]
- 2 Wang, 2011, Dynamic Control of Chiral Space in a Catalytic Asymmetric Reaction Using a Molecular Motor [DOI]
- 3 Liu, 2010, Recycling a Homogeneous Catalyst through a Light-Controlled Phase Tag [DOI]
- 4 Hecht, 2010, Artificial Light-Gated Catalyst Systems [DOI]
- 5 Chi, 2015, A Dual-Responsive Supra-Amphiphilic Polypseudorotaxane Constructed from a Water-Soluble Pillar [7] arene and an Azobenzene-Containing Random Copolymer [DOI]
- 6 Jochum, 2013, Temperature- and light-responsive smart polymer materials [DOI]
- 7 Pearson, 2010, Structural Optimization of Photoswitch Ligands for Surface Attachment of α-Chymotrypsin and Regulation of Its Surface Binding [DOI]
- 8 Matsumoto, 2008, Photo Gel–Sol/Sol–Gel Transition and Its Patterning ofa Supramolecular Hydrogel as Stimuli-Responsive Biomaterials [DOI]
- 9 Wyman, 1955, The cis-trans isomerization of conjugated compounds [DOI]
- 10 Bortolus, 1987, Cis-Trans Photoisomerization of Azobenzene-Cyclodextrin Inclusion Complexes [DOI]
- 11 Tamesue, 2010, Photoswitchable Supramolecular Hydrogels Formed by Cyclodextrins and Azobenzene Polymers [DOI]
- 12 Chen, 2013, Electrospun UV-responsive supramolecular nanofibers from a cyclodextrin–azobenzene inclusion complex [DOI]
- 13 Zhu, 2012, Photoswitchable Supramolecular Catalysis by Interparticle Host–Guest Competitive Binding [DOI]
- 14 Giordani, 2004, Photoinduced proton exchange between molecular switches [DOI]
- 15 Raymo, 2001, Signal Communication between Molecular Switches [DOI]
- 16 Berkovic, 2000, Spiropyrans and Spirooxazines for Memories and Switches [DOI]
- 17 Irie, 2014, Photochromism of Diarylethene Molecules and Crystals: Memories, Switches, and Actuators [DOI]
- 18 Bianchini, 2015, Photomodulable phosphines incorporating diarylethene moieties [DOI]
- 19 Neilson, 2013, Photoswitchable metal-mediated catalysis: Remotely tuned alkene and alkyne hydroborations
- 20 Neilson, 2011, Photoswitchable N-Heterocyclic Carbenes: Using Light to Modulate Electron-Donating Properties [DOI]
- 21 Roberts, 2009, Successful bifunctional photoswitching and electronic communication of two platinum (II) acetylide bridged dithienylethenes [DOI]
- 22 Samachetty, 2008, Modulating chemical reactivity using a photoresponsive molecular switch [DOI]
- 23 Samachetty, H.D., and Branda, N.R. (2005). Photomodulation of Lewis basicity in a pyridine-functionalized 1,2-dithienylcyclopentene. Chem. Commun., 2840–2842. [DOI]
- 24 Sud, 2005, Synthesis and Coordination Chemistry of a Photoswitchable Bis(phosphine) Ligand [DOI]
- 25 Vlasceanu, 2018, Photo/thermochromic macrocycles based on dihydroazulenes, dithienylethenes, and spiropyranes [DOI]
- 26 Szacilowski, 2008, Digital Information Processing in Molecular Systems [DOI]
- 27 Myles, 2002, 1,2-Dithienylethene Photochromes and Non-destructive Erasable Memory [DOI]
- 28 Fernandes, 2009, A photocontrolled molecular switch regulates paralysis in a living organism [DOI]
- 29 Yue, 2018, Recent Advances in Photoswitchable Cation Chemosensors [DOI]
- 30 Yao, 2014, A photochromic supramolecular polymer based on bis-p-sulfonatocalix [4] arene recognition in aqueous solution [DOI]
- 31 Mulder, A., Jukovic, A., Lucas, L.N., van Esch, J., Feringa, B.L., Huskens, J., and Reinhoudt, D.N. (2002). A dithienylethene-tethered β-cyclodextrin dimer as a photoswitchable host. Chem. Commun., 2734–2735. [DOI]
- 32 Bianchini, 2013, Efficient isonitrile hydration through encapsulation within a hexameric self-assembled capsule and selective inhibition by a photo-controllable competitive guest [DOI]
- 33 Takeshita, 1998, Photochromism of dithienylethenes included in cyclodextrins [DOI]
- 34 Takeshita, 2000, Photochromism of dithienylethene-bis(trimethylammonium) iodide in cyclodextrin cavities [DOI]
- 35 Ogino, 1981, Relatively High-Yield Syntheses of Rotaxanes. Syntheses and Properties of Compounds Consisting of Cyclodextrins Threaded by, -Diaminoalkanes Coordinated to Cobalt(III)- Complexes [DOI]
- 36 Harada, 2001, Cyclodextrin-based molecular machines [DOI]
- 37 Hashidzume, 2019, Cyclodextrin Based Rotaxanes: From Rotaxanes to Polyrotaxanes and Further to Functional Materials [DOI]
- 38 Zhang, 2018, Cyclodextrin Rotaxane with Switchable Pirouetting [DOI]
- 39 Pace, 2013, Enantioselective cyclization of photochromic dithienylethenes bound to DNA [DOI]
- 40 Li, 2018, Reversible Modulation of DNA-Based Hydrogel Shapes by Internal Stress Interactions [DOI]
- 41 Inoue, Y. (1993). Annual Reports on NMR Spectroscopy, Academic Press Limited.
- 42 Crini, 2014, A history of cyclodextrins [DOI]
- 43 2004, Cyclodextrins and their uses: A review
- 44 Hirose, 2001, A Practical Guide for the Determination of Binding Constants [DOI]
- 45 Dunitz, 1997, Organic fluorine hardly ever accepts hydrogen bonds [DOI]
- 46 Barbarich, 1999, Significant Inter- and Intramolecular O−H···FC Hydrogen Bonding [DOI]
- 47 Chaudhari, 2013, Engagement of CF3 Group in N–H···F–C Hydrogen Bond in the Solution State: NMR Spectroscopy and MD Simulation Studies [DOI]
- 48 Scheneider, 2012, Hydrogen bonds with fluorine. Studies in solution, in gas phase and by computations, conflicting conclusions from crystallographic analyses [DOI]
- 49 Nourmohammadian, 2011, A ‘chemically-gated’ photoresponsive compound as a visible detector for organophosphorus nerve agents [DOI]
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