15875-49-7Relevant articles and documents
Photoswitching using visible light: A new class of organic photochromic molecules
Helmy, Sameh,Leibfarth, Frank A.,Oh, Saemi,Poelma, Justin E.,Hawker, Craig J.,De Alaniz, Javier Read
, p. 8169 - 8172 (2014)
A versatile new class of organic photochromic molecules that offers an unprecedented combination of physical properties including tunable photoswitching using visible light, excellent fatigue resistance, and large polarity changes is described. These uniq
It's a Trap: Thiol-Michael Chemistry on a DASA Photoswitch
Alves, Jessica,Barner-Kowollik, Christopher,Blinco, James P.,Gr?fe, David,Walden, Sarah L.,Wiedbrauk, Sandra
, p. 809 - 813 (2020)
Donor–acceptor Stenhouse adducts (DASA) are popular photoswitches capable of toggling between two isomers depending on the light and temperature of the system. The cyclized polar form is accessed by visible-light irradiation, whereas the linear nonpolar f
New donor-acceptor stenhouse adducts as visible and near infrared light polymerization photoinitiators
Bonardi, Aude-Héloise,Dumur, Frédéric,Duval, Sylvain,Gigmes, Didier,Lalevée, Jacques,Noirbent, Guillaume,Xu, Yangyang
, (2020)
Polymerization photoinitiators that can be activated under low light intensity and in the visible range are being pursued by both the academic and industrial communities. To efficiently harvest light and initiate a polymerization process, dyes with high molar extinction coefficients in the visible range are ideal candidates. In this field, Donor-acceptor Stenhouse Adducts (DASA) which belong to a class of recently discovered organic photochromic molecules still lack practical applications. In this work, a series of DASA-based dyes are proposed as photoinitiators for the free radical polymerization of (meth)acrylates upon exposure to a near infrared light (laser diode at 785 nm).
Design and synthesis of donor-acceptor stenhouse adducts: A visible light photoswitch derived from furfural
Helmy, Sameh,Oh, Saemi,Leibfarth, Frank A.,Hawker, Craig J.,Read De Alaniz, Javier
, p. 11316 - 11329 (2014)
The development of an easily synthesized, modular, and tunable organic photoswitch that responds to visible light has been a long-standing pursuit. Herein we provide a detailed account of the design and synthesis of a new class of photochromes based on fu
Taming the complexity of donor-acceptor stenhouse adducts: Infrared motion pictures of the complete switching pathway
Zulfikri, Habiburrahman,Koenis, Mark A. J.,Lerch, Michael M.,Di Donato, Mariangela,Szymański, Wiktor,Filippi, Claudia,Feringa, Ben L.,Buma, Wybren Jan
, p. 7376 - 7384 (2019)
Switches that can be actively steered by external stimuli along multiple pathways at the molecular level are the basis for next-generation responsive material systems. The operation of commonly employed molecular photoswitches revolves around one key structural coordinate. Photoswitches with functionalities that depend on and can be addressed along multiple coordinates would offer novel means to tailor and control their behavior and performance. The recently developed donor-acceptor Stenhouse adducts (DASAs) are versatile switches suitable for such applications. Their photochemistry is well understood, but is only responsible for part of their overall photoswitching mechanism. The remaining thermal switching pathways are to date unknown. Here, rapid-scan infrared absorption spectroscopy is used to obtain transient fingerprints of reactions occurring on the ground state potential energy surface after reaching structures generated through light absorption. The spectroscopic data are interpreted in terms of structural transformations using kinetic modeling and quantum chemical calculations. Through this combined experimental-theoretical approach, we are able to unravel the complexity of the multidimensional ground-state potential energy surface explored by the photoswitch and use this knowledge to predict, and subsequently confirm, how DASA switches can be guided along this potential energy surface. These results break new ground for developing user-geared DASA switches but also shed light on the development of novel photoswitches in general.
Properties of a furan ring-opening reaction in aqueous micellar solutions for selective sensing of mesalazine
Sabahi-Agabager, Leila,Eskandari, Habibollah,Nasiri, Farough,Shamkhali, Amir Nasser,Baghi Sefidan, Somayyeh
, (2021)
A novel and efficient non-azo formation based method was developed for trace sensing of mesalazine (MES), a pharmaceutical aromatic amine. MES was simply coupled with a Meldrum's activated furan (MAF) reagent via a furan ring opening reaction to form a colored product. The intense purple colored solution was detected at 575 nm. The reaction of MES with MAF was monitored by employing 1H NMR spectroscopy and mass spectrometry. In addition, density functional theory (DFT) was applied to optimize the structure of the colored product and its λmax (the wavelength of maximum absorbance) in dimethyl sulfoxide and water. The colored product was considered in three possible structures, and the most possible structures in dimethyl sulfoxide and in water were identified by employing the DFT calculations. Both of the most possible structures indicated only a local excitation in their λmax and no charge transfer was observed. However, one of the structures in dimethyl sulfoxide presented charge transfer properties occurring through N–C[dbnd]C–C moiety. A univariate optimization method was also used to attain the optimum condition for analysis. In addition, the dependence of the analytical response on the three main affecting parameters (reaction time (X1), Triton X-100 concentration (X2) and MAF concentration (X3)) was identified by employing a central composite design (CCD) approach. The CCD study showed that the analytical response depends complexly on the parameters. Beer's law was obeyed within the range of 0.06–9.30 μg mL?1 of MES (155 fold linearity) at 575 nm, under the optimum condition introduced by the CCD approach. Also, the limit of detection was obtained 0.04 μg mL?1 of MES. The method showed precision (as relative standard deviation) and accuracy (as recovery) within the ranges of 0.6–3.2 % and 96.3–100.8%, respectively. Various organic and inorganic species, amino-pharmaceuticals, and amino acids were tested to evaluate the selectivity of the method. The selectivity of the analytical method was satisfactory. The method was successfully applied for detection of MES in various water matrices and pharmaceutical tablets.
Promoting the Furan Ring-Opening Reaction to Access New Donor–Acceptor Stenhouse Adducts with Hexafluoroisopropanol
Clerc, Michèle,Stricker, Friedrich,Ulrich, Sebastian,Sroda, Miranda,Bruns, Nico,Boesel, Luciano F.,Read de Alaniz, Javier
supporting information, p. 10219 - 10227 (2021/03/22)
Donor–acceptor Stenhouse adducts (DASAs) are visible-light-responsive photoswitches with a variety of emerging applications in photoresponsive materials. Their two-step modular synthesis, centered on the nucleophilic ring opening of an activated furan, ma
