31241-19-7Relevant articles and documents
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.
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.
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.
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.
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.
Light-Switchable Buffers
Berton, Cesare,Busiello, Daniel Maria,Fadaei-Tirani, Farzaneh,Pezzato, Cristian,Scopelliti, Rosario,Severin, Kay,Zamuner, Stefano
supporting information, p. 21737 - 21740 (2021/08/26)
A visible light-switchable buffer system based on a merocyanine photoacid is presented. Para-substitution of the indolium side with a methoxy group affords a compound suitable for making hydrolytically stable aqueous buffers whose pH can be tuned between 7 and 4 using 500 nm light.
