Intra- and Intermolecular Hydrogen Bonds in Pyrrolylindandione Derivatives and Their Interaction with Fluoride and Acetate: Possible Anion Sensing Properties

Sigalov, M. V.; Shainyan, B. А.; Chípanina, N. N.; Oznobikhina, Larisa P.

doi:10.1021/jp4072179

Cited by 23 publications

(12 citation statements)

References 16 publications

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“…In this article, an extended version of the well-known indane-1,3-dione, i.e., 1 H -cyclopenta[ b ]naphthalene-1,3(2 H )-dione EA4 , has been used for the design of ten push-pull dyes. It has to be noticed that even if the synthesis of EA4 is reported in the literature since 2006 [28], only one report mentions the development of anion sensors with EA4 in 2013 [29] and the first push-pull dyes have been developed in 2017 for photovoltaics applications [30,31]. Considering the scarcity of studies devoted to this electron acceptor, a series of 10 push-pull chromophores PP1 – PP10 have been developed with EA4 .…”

Section: Introductionmentioning

confidence: 99%

Push-Pull Chromophores Based on the Naphthalene Scaffold: Potential Candidates for Optoelectronic Applications

et al. 2019

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A series of ten push-pull chromophores comprising 1H-cyclopenta[b]naphthalene-1,3(2H)-dione as the electron-withdrawing group have been designed, synthesized, and characterized by UV-visible absorption and fluorescence spectroscopy, cyclic voltammetry and theoretical calculations. The solvatochromic behavior of the different dyes has been examined in 23 solvents and a positive solvatochromism has been found for all dyes using the Kamlet-Taft solvatochromic relationship, demonstrating the polar form to be stabilized in polar solvents. To establish the interest of this polyaromatic electron acceptor only synthesizable in a multistep procedure, a comparison with the analog series based on the benchmark indane-1,3-dione (1H-indene-1,3(2H)-dione) has been done. A significant red-shift of the intramolecular charge transfer band has been found for all dyes, at a comparable electron-donating group. Parallel to the examination of the photophysical properties of the different chromophores, a major improvement of the synthetic procedure giving access to 1H-cyclopenta[b]naphthalene-1,3(2H)-dione has been achieved.

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Section: Introductionmentioning

confidence: 99%

Push-Pull Chromophores Based on the Naphthalene Scaffold: Potential Candidates for Optoelectronic Applications

et al. 2019

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“…The transition from the 1 H - to 2 H -form in going from 8 to 6 is also proved by the 4.4 ppm downfield shift of the NH proton resonance, from 11.1 to 15.5 ppm (Figure a), suggesting the formation of a fairly strong N–H···O intramolecular H-bond (Scheme ), ,,, which is possible only in the 6 -2 H tautomer.…”

Section: Resultsmentioning

confidence: 97%

2H-Indazole Tautomers Stabilized by Intra- and Intermolecular Hydrogen Bonds

et al. 2019

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2-[(2H-Indazol-3-yl)methylene]-1H-indene-1,3(2H)-dione 6 and (E)-2-[(2H-indazol-3-yl)methylene]-2,3-dihydro-1H-inden-1-one 7 have been synthesized. In the crystal, the NH hydrogen atom of 6 is disordered between the N(1) and N(2) atoms with the population ratio of 0.69:0.31. Molecule 7 crystallizes in two tautomeric polymorphs: 7-1H tautomer (yellow) and 7-2H tautomer (red). Both 6 and 7 form centrosymmetric dimers in the crystal with the monomeric units linked by COAccording to 1 H and 13 C NMR data, in DMSO-d 6 solution, the 6-1H tautomer predominates, whereas in less polar CDCl 3 or CD 2 Cl 2 , the 6-2H tautomer is stabilized by a strong N−H•••OC intramolecular hydrogen bond. Compound 7 in dimethyl sulfoxide (DMSO) or ethanol solutions exists in the form of 7-1H and 7-2H tautomers. On the example of the 7-2H tautomer, it was shown for the first time that the 2H tautomers of 3-substituted indazoles can be stabilized by an intermolecular hydrogen bond and may remain in aprotic solvents almost indefinitely. However, in the open air or in water, fast 2H → 1H tautomerization occurs. As follows from density functional theory calculations, the high stability of the 2H form in solution is due to the formation of centrosymmetric dimers, which are more stable than the corresponding dimers of the 1H tautomer.

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“…Noticeably, examples of dyes based on 1H-cyclopentanaphthalene-1,3-dione are extremely scarce in literature [42,[54][55][56][57], evidencing the interest and the novelty of the structures proposed in this work. Interestingly, their good light absorption properties @405 nm were anticipated by theoretical calculations and molecular design.…”

Section: Introductionmentioning

confidence: 95%

Free Radical Photopolymerization and 3D Printing Using Newly Developed Dyes: Indane-1,3-Dione and 1H-Cyclopentanaphthalene-1,3-Dione Derivatives as Photoinitiators in Three-Component Systems

et al. 2020

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The design of photoinitiating systems with excellent photochemical reactivities at 405nm LED is one of the obstacles to efficiently promote free radical polymerization in mild conditions (e.g., low light intensity, under air). Here, our actual search for new multicomponent photoinitiating systems at 405nm LED prompts us to develop new dyes based on push–pull structures. In the present paper, we chose two series of new dyes which possess indane-1,3-dione and 1H-cyclopenta naphthalene-1,3-dione groups as the electron-withdrawing groups, since they have the great potential to behave as sensitive and remarkable photoinitiators in vat photopolymerization/3D printing. When incorporated with a tertiary amine (ethyl dimethylaminobenzoate EDB, used as electron/hydrogen donor) and an iodonium salt (used as electron acceptor) as the three-component photoinitiating systems (PISs), and among a series of 21 dyes, 10 of them could efficiently promote the free radical photopolymerization of acrylates. Interestingly, steady state photolysis experiments revealed different behaviors of the dyes. Fluorescence experiments and free energy change calculations for redox processes were also carried out to investigate the relevant chemical mechanisms. Additionally, the formation of radicals from the investigated PISs was clearly observed by electron spin resonance (ESR) spin-trapping experiments. Finally, stereoscopic 3D patterns were successfully fabricated by the laser writing technique. In this work, the use of push–pull dyes based on the naphthalene scaffold as photoinitiators of polymerization is reported for the first time in a systematic study aiming at investigating the structure–performance relationship for irradiation carried out at 405 nm. By carefully selecting the electron donors used in the two series of push–pull dyes, novel and high-performance photoinitiating systems operating at 405 nm are thus proposed.

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Intra- and Intermolecular Hydrogen Bonds in Pyrrolylindandione Derivatives and Their Interaction with Fluoride and Acetate: Possible Anion Sensing Properties

Cited by 23 publications

References 16 publications

Push-Pull Chromophores Based on the Naphthalene Scaffold: Potential Candidates for Optoelectronic Applications

Push-Pull Chromophores Based on the Naphthalene Scaffold: Potential Candidates for Optoelectronic Applications

2H-Indazole Tautomers Stabilized by Intra- and Intermolecular Hydrogen Bonds

Free Radical Photopolymerization and 3D Printing Using Newly Developed Dyes: Indane-1,3-Dione and 1H-Cyclopentanaphthalene-1,3-Dione Derivatives as Photoinitiators in Three-Component Systems

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