16650-15-0Relevant academic research and scientific papers
Femtosecond UV/mid-IR study of photochromism of the spiropyran 1′,3′-dihydro-1′,3′,3′-trimethyl-6- nitrospiro[2H-1-benzopyran-2,2′-(2H)-indole] in solution
Holm, Ann-Kathrin,Rini, Matteo,Nibbering, Erik T.J.,Fidder, Henk
, p. 214 - 219 (2003)
The ring-opening reaction of 1′,3′- dihydro-1′,3′,3′- trimethyl-6-nitrospiro[2H-1-benzopyran-2,2′-(2H)-indole] is investigated in two solvents, by probing the evolution of the vibrational absorption spectrum with 130 fs time-resolution. Competition betwee
Kinetic Studies of Solvent and Pressure Effects on Thermochromic Behavior of 6-Nitrospiropyran
Sueishi, Yoshimi,Ohcho, Masanobu,Nishimura, Norio
, p. 2608 - 2613 (1985)
The thermal conversion of 6-nitrospiropyran from a merocyanine form to a spiro form was studied in various solvents and under high pressures.The rates of the thermal conversions were remarcably retarded in polar solvents, and a Kirkwood plot of the rate c
Distinct influence of the anion and ether group on the polarity of ammonium and imidazolium ionic liquids
Zhang, Shiguo,Chen, Zhengjian,Qi, Xiujuan,Deng, Youquan
, p. 1043 - 1050 (2012)
The polarity of ionic liquids (ILs), usually denoted as ET(30) by the solvatochromic probe Reichardt's dye, is one of the most fundamental properties that remarkably affect the solvation and chemical reaction in ILs. It was generally accepted that the ET(30) of ILs was dominated by the nature of the cation. However, in this work, it was found that the common ammonium-based ILs showed strongly anion-dependent ET(30). For example, the ET(30) value for [N1124][DCA] and [N 1124][NTf2] is 49.0 and 59.0 kcal mol-1, respectively, while the corresponding imidazolium ILs bearing the same anions possess nearly identical ET(30), the ET(30) value for [BMIm][DCA] and [BMIm][NTf2] is 51.4 and 51.6 kcal mol-1, respectively. Moreover, introduction of an ether group was found to increase the ET(30) of imidazolium ILs while having no obvious effect on that of ammonium-based ILs. The Kamlet-Taft parameters and density functional theory (DFT) calculations indicated that the distinct result is related to different stabilization of the ground state of Reichardt's dye 30. In imidazolium ILs, the main interactions between ILs and zwitterionic dye involve both coulombic interaction (between the cation and the phenolate oxygen atom) and H-bonding interaction (between the acidic hydrogen on imidazolium ring and the phenolate oxygen atom). However, with the ammonium ILs lack of active hydrogen, the dye is only stabilized by the coulombic interaction between the cation and the phenolate oxygen atom. Interestingly, in both imidazolium and ammonium-based ILs, the spiropyran-merocyanine equilibrium exhibit obvious anion-dependent photochromism, solvatochromism, and thermal relaxation. The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2012.
The Role of Large Conformational Changes in Efficient Ultrafast Internal Conversion: Deviations from the Energy Gap Law
Fidder, Henk,Rini, Matteo,Nibbering, Erik T. J.
, p. 3789 - 3794 (2004)
Conversion of electronic excitation energy into vibrational energy was investigated for photochromic spiropyran molecules, using femtosecond UV-mid-IR pump-probe spectroscopy. We observe a weaker energy gap dependence than demanded by the "energy gap law"
Reversing the thermal stability of a molecular switch on a gold surface: Ring-opening reaction of nitrospiropyran
Piantek, Marten,Schulze, Gunnar,Koch, Matthias,Franke, Katharina J.,Leyssner, Felix,Krueger, Alex,Navio, Cristina,Miguel, Jorge,Bernien, Matthias,Wolf, Martin,Kuch, Wolfgang,Tegeder, Petra,Pascual, Jose Ignacio
, p. 12729 - 12735 (2009)
The ring-opening/closing reaction between spiropyran (SP) and merocyanine (MC) is a prototypical thermally and optically induced reversible reaction. However, MC molecules in solution are thermodynamically unstable at room temperature and thus return to t
Colorimetric response of spiropyran derivative for anions in aqueous or organic media
Shiraishi, Yasuhiro,Itoh, Masataka,Hirai, Takayuki
, p. 891 - 897 (2011)
We previously found that a simple spiropyran derivative (1:1′,3′,3′-trimethyl-6-nitro-spiro-[2H-1-benzopyran-2, 2′-indoline]) behaves as a selective and sensitive cyanide anion (CN -) receptor in aqueous media under UV irradiation13.
Spiropyran-conjugated thermoresponsive copolymer as a colorimetric thermometer with linear and reversible color change
Shiraishi, Yasuhiro,Miyamoto, Ryo,Hirai, Takayuki
, p. 1571 - 1574 (2009)
A simple copolymer, poly(NIPAM-co-SP), consisting of N-isopropylacrylamide and spiropyran units, behaves as a colorimetric thermometer exhibiting temperature-responsive linear and reversible bathochromic/hypsochromic shift of the absorption spectra under
Photoswitching and sensor applications of a spiropyran-polythiophene conjugate
Park, In Sung,Jung, Young-Sik,Lee, Kee-Jung,Kim, Jong-Man
, p. 2859 - 2861 (2010)
A new FRET-based, photoswitchable fluorescent dyad derived from a spiropyran-polythiophene conjugate was developed and applied to the detection of cyanide anion.
Synthesis, optical properties and in vitro cell viability of novel spiropyrans and their photostationary states
Rastogi, Shiva K.,Zhao, Zhenze,Gildner, M. Brenton,Shoulders, Ben A.,Velasquez, Tara L.,Blumenthal, Madeleine O.,Wang, Lei,Li, Xiaopeng,Hudnall, Todd W.,Betancourt, Tania,Du, Liqin,Brittain, William J.
, (2021/01/06)
A novel class of spiropyran (SP) was synthesized using a multistep process that involves three key intermediates: (a) diazonium-tetrafluoroborate, (b) hydrazine and (c) indolium iodide. Single crystal X-ray spectroscopy was used to confirm the structure of one of the analogues. The SP analogues were confirmed as being able to isomerize and attain a photostationary state (PSS) upon irradiation with ultraviolet light (UV, 365 nm) in an aqueous environment. UV–visible absorption spectra were recorded to confirm the isomerization properties. The ability of the synthesized compounds to induce growth inhibition of HeLa cervical cancer cells was assessed via the MTT assay after incubation with either the SP or their PSS. The IC50 values of two PSS (PSS-2, 4), were observed to be around 14 ± 4 fold lower (26 ± 3 μM) than their corresponding SPs. The most cytotoxic compounds SP-7 and PSS-7 showed the lowest IC50 values (12 μM). An in vitro tubulin polymerization assay showed that SP-7 and PSS-7 exhibited the greatest difference in tubulin inhibition relative to unirradiated SP-1 and SP-4.
Conductance Photoswitching of Metal–Organic Frameworks with Embedded Spiropyran
Garg, Shubham,Schwartz, Heidi,Kozlowska, Mariana,Kanj, Anemar Bruno,Müller, Kai,Wenzel, Wolfgang,Ruschewitz, Uwe,Heinke, Lars
supporting information, p. 1193 - 1197 (2019/01/04)
Conductive metal–organic frameworks (MOFs) as well as smart, stimuli-responsive MOF materials have attracted considerable attention with respect to advanced applications in energy harvesting and storage as well as in signal processing. Here, the conductance of MOF films of type UiO-67 with embedded photoswitchable nitro-substituted spiropyrans was investigated. Under UV irradiation, the spiropyran (SP) reversibly isomerizes to the open merocyanine (MC) form, a zwitterionic molecule with an extended conjugated π-system. The light-induced SP–MC isomerization allows for remote control over the conductance of the SP@UiO-67 MOF film, and the conductance can be increased by one order of magnitude. This research has the potential to contribute to the development of a new generation of photoelectronic devices based on smart hybrid materials.
