31241-19-7Relevant academic research and scientific papers
Synthesis, crystal structure and photochromism of a novel spiro[indoline-naphthaline]oxazine derivative
Li, Hong,Pang, Meili,Wu, Bianpeng,Meng, Jiben
, p. 23 - 29 (2015)
A new spiro[indoline-naphthaline]oxazine derivative, 12-methoxy-14,14-dimethyl-17-(piperidin-1-yl)-7,8,14,15a-tetrahydro-4bH-naphtho[1″,2″:5′,6′][1,4]oxazino[3′,2′:2,3][1,4]oxazino[4,3-a]indole (1), was successfully synthesized, and its structure was characterized by 1H NMR, 13C NMR, IR, HRMS and single-crystal X-ray diffraction method. X-ray diffraction indicates that benzene and naphthalene rings of compound 1 are almost perpendicular, and the piperidine ring at the 6′-C site is in a chair conformation. In the packing diagram, a couple of short intermolecular distances such as the intermolecular short contact are observed. The photochromic properties of compound 1 have been fully investigated in different solvents, it was found that it exhibited excellent photochromism properties in solvents.
Cyanine-Flavonol Hybrids for Near-Infrared Light-Activated Delivery of Carbon Monoxide
?tacková, Lenka,Russo, Marina,Muchová, Lucie,Orel, Vojtěch,Vítek, Libor,?tacko, Peter,Klán, Petr
, p. 13184 - 13190 (2020)
Carbon monoxide (CO) is an endogenous signaling molecule that controls a number of physiological processes. To circumvent the inherent toxicity of CO, light-activated CO-releasing molecules (photoCORMs) have emerged as an alternative for its administration. However, their wider application requires photoactivation using biologically benign visible and near-infrared (NIR) light. In this work, a strategy to access such photoCORMs by fusing two CO-releasing flavonol moieties with a NIR-absorbing cyanine dye is presented. These hybrids liberate two molecules of CO in high chemical yields upon activation with NIR light up to 820 nm and exhibit excellent uncaging cross-sections, which surpass the state-of-the-art by two orders of magnitude. Furthermore, the biocompatibility and applicability of the system in vitro and in vivo are demonstrated, and a mechanism of CO release is proposed. It is hoped that this strategy will stimulate the discovery of new classes of photoCORMs and accelerate the translation of CO-based phototherapy into practice.
Photomodulation of the electrode potential of a photochromic spiropyran-modified Au electrode in the presence of Zn2+: A new molecular switch based on the electronic transduction of the optical signals
Wen, Guoyong,Yan, Jie,Zhou, Yucheng,Zhang, Deqing,Mao, Lanqun,Zhu, Daoben
, p. 3016 - 3018 (2006)
The electrode potential of a photochromic spiropyran-modified Au electrode could be reversibly modulated by UV/visible light irradiation in the presence of Zn2+, and a new molecular switch and an AND logic gate based on this electronic transduction of the optical signals were established. The Royal Society of Chemistry 2006.
The synthesis of 6-substituted pyrido[2,3-d]pyrimidine-2,4(1H,3H)-diones using aminomethylene malondialdehydes and 6-aminouracils
Rashidi,Baradarani,Joule
, p. 1068 - 1072 (2014)
Variously substituted aminomethylene malondialdehydes (2-(3,3- dimethylindolin-2-ylidene)malondialdehydes) were reacted with some 6-aminouracils, to give 6-(3,3-dimethyl-3H-indol-2-yl)pyrido[2,3-d]pyrimidine-2, 4-(1H,3H)-diones in good yields.
Newly synthesized indolium-based ionic liquids as unprecedented inhibitors for the corrosion of mild steel in acid medium
Ahmed, Saleh A.,Awad, Mohamed I.,Althagafi, Ismail I.,Altass, Hatem M.,Morad, Moataz,Alharbi, Ahmed,Obaid, Rami J.
, (2019)
New indolium-based ionic liquids (IBILs) of chemical formula 5-methoxy-1,2,3,3-tetramethyl-3H-indolium iodide (IBIL-I), 1-(2-carboxyethyl)-2,3,3-trimethyl-3H-indolium iodide (IBIL-II), 2,3,3-trimethyl-1-(pyren-2-ylmthyl)-3H-indolium iodide (IBIL-III), 1-(3-ethoxy-3-oxopropyl)-2,3,3-trimethyl-3H-indolium bromide (IBIL-IV) and 1-(2-ethoxy-2-oxoethyl)-2,3,3-trimethyl-3H-indolium bromide (IBIL-V) have been synthesized and characterized. The adsorption and corrosion inhibition effect of those IBILs have been studied using polarization measurements and cyclic voltammetry. It has been found that the inhibitive effect of the corrosion of mild steel in 0.5 M H2SO4 is inherently dependent on the structure of the studied IBILs; IBILs with bromide as an anionic head are more efficient than those with iodide. Thermodynamic calculations indicated that the adsorption on steel surface accords with Langmuir adsorption isotherm. Electrochemical measurements showed that the IBIL-IV, with the highest inhibition efficiency, acted mainly as a mixed type inhibitor, albeit the inhibition of the anodic branch is larger than the cathodic one. Cyclic voltammetric measurements at polycrystalline gold electrode gave an insight into the mechanism of corrosion inhibition by the studied ionic liquids.
Kinetic competition in liquid electrolyte and solid-state cyanine dye sensitized solar cells
Tatay, Sergio,Haque, Saif A.,O'Regan, Brian,Durrant, James R.,Verhees,Kroon,Vidal-Ferran,Gavina, Pablo,Palomares, Emilio
, p. 3037 - 3044 (2007)
The photovoltaic performance of liquid electrolyte and solid-state dye sensitized solar cells, employing a squarilium methoxy cyanide dye, are evaluated in terms of interfacial electron transfer kinetics. Dye adsorption to the metal oxide film resulted in a mixed population of aggregated and monomeric sensitizer dyes. Emission quenching data, coupled with transient absorption studies, indicate that efficient electron injection was only achieved by the monomeric dyes, with the aggregated dye population having an injection yield an order of magnitude lower. In liquid electrolyte devices, transient absorption studies indicate that photocurrent generation is further limited by slow kinetics of the regeneration of monomeric dye cations by the iodide/iodine redox couple. The regeneration dynamics are observed to be too slow (? 100 s) to compete effectively with the recombination of injected electrons with dye cations. In contrast, for solid-state devices employing the organic hole conductor spiro-OMeTAD, the regeneration dynamics are fast enough (? 1 s) to compete effectively with this recombination reaction, resulting in enhanced photocurrent generation. The Royal Society of Chemistry.
Optimizing the framework of indolium hemicyanine to detect sulfur dioxide targeting mitochondria
Chao, Jianbin,Huo, Fangjun,Wang, Zhuo,Zhang, Ting,Zhang, Yongbin
supporting information, (2021/10/04)
Endogenous sulfur dioxide (SO2) is mainly produced by the enzymatic reaction of sulfur-containing amino acids in mitochondria, which has unique biological activity in inflammatory reaction, regulating blood pressure and maintaining the homeostasis of biological sulfur. It is more and more common to detect monitor SO2 levels by fluorescence probe. In recent years, the indolium hemicyanine skeleton based on the D-π-A structure has been widely used in the development of fluorescent sensors for the detection of SO2. However, subtle changes in the chemical structure of indolium may cause significant differences in SO2 sensing behavior. In this article, we designed and synthesized two probes with different lipophilicities to further study the relationship between the structure and optical properties of hemicyanine dyes. On the basis of previous studies, the structure of indolium hemicyanine skeleton was optimized by introducing –OH group, so that MC-1 and MC-2 had the best response to SO32- in pure PBS system. In addition, the lipophilicity of MC-2 was better than that of MC-1, which enabled it to respond quickly to SO32- and better target mitochondria for SO2 detection. Most importantly, the low detection limits of MC-1 and MC-2 conducive to the detection of endogenous SO2. This work provided an idea for developing SO2 fluorescent sensors with excellent water solubility and low detection limit.
Programmable Chromism and Photoluminescence of Spiropyran-Based Liquid Crystalline Polymer with Tunable Glass Transition Temperature
Hu, Wei,Qin, Shengyu,Ren, Yunxiao,Shao, Yu,Sun, Chang,Wang, Qian,Wu, Yu,Yang, Dengke,Yang, Huai,Zhang, Lanying
supporting information, p. 19406 - 19412 (2021/08/06)
Spiropyran-based materials (SPBMs) can give responses to the stimulations induced by the light, heat, force, or pH, which have been used as triggers for many smart materials. Here, a cross-linkable SPBM containing mesogenic-units is synthesized, which is pale-colored, non-photoluminescent and non-mesogenic at a spiro form, but dark-colored, photoluminescent, and mesogenic at a merocyanine form. Moreover, the dynamic interconversion behavior of the form in the different chemical environments are distinct. Liquid crystalline polymers (LCPs) containing the SPBMs cross-linked via visible light, own a photoswitchable glass transition temperature (Tg) and retain the switchable property; however, the SPBMs cross-linked via UV light will be locked at the MC state, because the molecular movement was frozen at the room temperature lower than the given Tg of the LCP. Thus, programmable chromism and photoluminescence based on the tunable Tg can be endowed to the functional materials prepared from the SPBMs.
Fast, reversible mechanochromism of regioisomeric oxazine mechanophores: Developing in situ responsive force probes for polymeric materials
Qian, Hai,Purwanto, Nathan S.,Ivanoff, Douglas G.,Halmes, Abigail J.,Sottos, Nancy R.,Moore, Jeffrey S.
supporting information, p. 1080 - 1091 (2021/04/19)
To address hysteretic or irreversible mechanochromism found in most bond-scission-based mechanophores, we developed a new family of mechanophores based on the oxazine (OX) structural motif. Three OX regioisomers differing in their point of attachment to the indole ring show variable mechanochromic mechanoresponsiveness in a polydimethylsiloxane (PDMS) matrix. Constrained DFT simulations correlate the experimental findings to molecular scale events; two of the three regioisomers exhibit a force-activated rearrangement, while the third one is mechanochemically inactive. Most significantly, when compared with the spiropyran (SP) and the naphthopyran (NP), the OX mechanophores exhibit faster and reversible mechanochromism without any sign of fatigue. Such a rapid response to mechanical loads is rationalized by the difference between SP and OX scaffolds, given that the SP ring opening is accompanied by a trans-cis isomerization step. These fast-responsive mechanophores are anticipated to bring deeper understanding to a broad range of soft materials by in situ monitoring the local mechanics.
Large, Tunable, and Reversible pH Changes by Merocyanine Photoacids
Andreásson, Joakim,Beves, Jonathon E.,Peeks, Martin D.,Prasad, Shyamal K. K.,Schmidt, Timothy W.,Wimberger, Laura
supporting information, p. 20758 - 20768 (2021/12/14)
Molecular photoswitches capable of generating precise pH changes will allow pH-dependent processes to be controlled remotely and noninvasively with light. We introduce a series of new merocyanine photoswitches, which deliver reversible bulk pH changes up to 3.2 pH units (pH 6.5 to pH 3.3) upon irradiation with 450 nm light, displaying tunable and predictable timescales for thermal recovery. We present models to show that the key parameters for optimizing the bulk pH changes are measurable: the solubility of the photoswitch, the acidity of the merocyanine form, the thermal equilibrium position between the spiropyran and the merocyanine isomers, and the increased acidity under visible light irradiation. Using ultrafast transient absorption spectroscopy, we determined the quantum yields for the ring-closing reaction and found that the lifetimes of the transient cis-merocyanine isomers ranged from 30 to 550 ns. Quantum yields did not appear to be a limitation for bulk pH switching. The models we present use experimentally determined parameters and are, in principle, able to predict the change in pH obtained for any related merocyanine photoacid.
