X-Ray Structures of Electrochromic Compounds. Colorless 3,3-Dimethyl-2-(<i>p</i>-dimethylaminostyryl)indolino-[1,2-<i>b</i>]oxazoline and Colored 2-(p-Dimethylaminostyryl)-1-hydroxyethyl-3,3-dimethylindolinium Bromide

Kawami, Satoshi; Yoshioka, Hiroshi; Nakatsu, Kazumi; Okazaki, Tsuneki; Hayami, Masaaki

doi:10.1246/cl.1987.711

Cited by 14 publications

(7 citation statements)

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“…[11] Electroaddressability of the BOX unit was also evidenced, subjectt o substitution on the indoline part and to the nature of the associateds tyrylic moiety. [4,12,13] As illustrated in Scheme 1, combining the DTE and BOX subunits through an ethylenic bridge that can undergo Z/E isomerization gives rise to eights tates. The changes in the absorption spectra,c haracterizedi na cetonitrile along the different pathways,d emonstrated that each of these states had au nique spectral signature.…”

Section: Introductionmentioning

confidence: 99%

Second‐Order Nonlinear Optical Properties of a Dithienylethene–Indolinooxazolidine Hybrid: A Joint Experimental and Theoretical Investigation

Bondu

Quertinmont

Rodriguez

et al. 2015

Chemistry A European J

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The nonlinear optical (NLO) properties of a double photochrome molecular switch are reported for the first time by considering the four trans forms of a dithienylethene-indolinooxazolidine hybrid. The four forms are characterized by means of hyper-Rayleigh scattering (HRS) experiments and quantum chemical calculations. Experimental measurements provide evidence that the pH- and light-triggered transformations between the different forms of the hybrid are accompanied by large variations of the first hyperpolarizability, which makes this compound an effective multistate NLO switch. Quantum chemical calculations conducted at the time-dependent Hartree-Fock and time-dependent DFT levels agree with the experimental data and allow a complete rationalization of the NLO responses of the different forms. The HRS signal of the forms with an open indolinooxazolidine moiety are more than one order of magnitude larger than that measured for the other forms, whereas the open/closed status of the dithienylethene subunit barely influences the dynamic NLO properties. However, extrapolation of the NLO responses to the static limit leads to univocally distinguishable intrinsic responses for three of the various forms. This hybrid system thus acts as a highly efficient multistate NLO switch for eventual exploitation in optical memory systems with multiple storage and nondestructive readout capacity.

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Section: Introductionmentioning

confidence: 99%

Second‐Order Nonlinear Optical Properties of a Dithienylethene–Indolinooxazolidine Hybrid: A Joint Experimental and Theoretical Investigation

Bondu

Quertinmont

Rodriguez

et al. 2015

Chemistry A European J

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“…Optimized structures and corresponding Gibbs free energies for the most stable conformer of each BOX isomer are presented in Figure and summarized in Table , respectively. Our computational results for the trans-isomers show that the optimized geometries for Ct and Ot are very close to those previously reported in experimental and theoretical studies of related compounds. In the Ct form, the asymmetric carbon lies slightly out of the plane of the indoline and features a sp 3 hybridization that leads to a globally distorted structure.…”

Section: Resultsmentioning

confidence: 99%

Indolino-Oxazolidine Acido- and Photochromic System Investigated by NMR and Density Functional Theory Calculations

et al. 2018

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Three addressable indolino-oxazolidine units connected through an isomerizable double bond to a substituted thiophene represent a smart example of a multiaddressable system whose reversible responses could be selectively activated on demand. Experimental and theoretical approaches to push forward the understanding of the system mechanism and set pathways to design optimized compounds for suitable application are here presented. NMR and UV-visible spectroscopies are used for structural and kinetic studies, while density functional theory (DFT) calculations pave the way to highlight energetic and electronic processes that are involved. Substitution and solvent effects toward the reactivity of the compounds are experimentally studied and combined with theoretical calculations. The most efficient and selective stimuli to travel between the four possible states resulting from the ring-opening of indolino[2,1- b]oxazolidine (generally referenced as BOX) derivatives and the trans-cis isomerization of the ethylenic junction are elucidated.

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“…The successive addition of some acid aliquots revealed an isosbestic point evidencing that the oxazolidine ring opening did not occur in a stepwise manner. Indeed, under their closed forms, the indoline heterocycles are generally almost orthogonal to their olefinic substituent [15][16]. As a consequence, no interaction through bonds between them could be expected leading to an independent behavior and then a concomitant commutation of them when the indolinooxazolidine units, hereafter named BOX for convenience, are directly stimulated.…”

Section: Investigations Of Processes Between All-trans Isomers Of Tarmentioning

confidence: 99%

13 metastable states arising from a simple multifunctional unimolecular system

et al. 2017

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HAL is a multidisciplinary open access archive for the deposit and dissemination of scientific research documents, whether they are published or not. The documents may come from teaching and research institutions in France or abroad, or from public or private research centers. L'archive ouverte pluridisciplinaire HAL, est destinée au dépôt et à la diffusion de documents scientifiques de niveau recherche, publiés ou non, émanant des établissements d'enseignement et de recherche français ou étrangers, des laboratoires publics ou privés.

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X-Ray Structures of Electrochromic Compounds. Colorless 3,3-Dimethyl-2-(p-dimethylaminostyryl)indolino-[1,2-b]oxazoline and Colored 2-(p-Dimethylaminostyryl)-1-hydroxyethyl-3,3-dimethylindolinium Bromide

Cited by 14 publications

References 1 publication

Second‐Order Nonlinear Optical Properties of a Dithienylethene–Indolinooxazolidine Hybrid: A Joint Experimental and Theoretical Investigation

Second‐Order Nonlinear Optical Properties of a Dithienylethene–Indolinooxazolidine Hybrid: A Joint Experimental and Theoretical Investigation

Indolino-Oxazolidine Acido- and Photochromic System Investigated by NMR and Density Functional Theory Calculations

13 metastable states arising from a simple multifunctional unimolecular system

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