CNNC conformational isomers of 2′-hydroxyacetophenone azine: FTIR matrix isolation and DFT study

Grzegorzek, Joanna; Mielke, Zofia; Filarowski, Aleksander

doi:10.1016/j.molstruc.2010.04.017

Cited by 14 publications

(19 citation statements)

References 28 publications

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“…This stereochemistry is consistent with that previously reported for symmetrical and unsymmetrical aromatic azines [15,19]. Selected bond lengths (Å): C1-C6, 1.461 (7); C6-N1, 1.279 (7); N1-N2, 1.406(5); N2-C7, 1.257(8);…”

Section: Accepted Manuscriptsupporting

confidence: 91%

Unsymmetrical cyrhetrenyl and ferrocenyl azines derived from 5-nitrofurane: Synthesis, structural characterization and electrochemistry

Gómez

Klahn

Fuentealba

et al. 2015

Inorganic Chemistry Communications

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Section: Accepted Manuscriptsupporting

confidence: 91%

Unsymmetrical cyrhetrenyl and ferrocenyl azines derived from 5-nitrofurane: Synthesis, structural characterization and electrochemistry

Gómez

Klahn

Fuentealba

et al. 2015

Inorganic Chemistry Communications

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“…In HEX, the ground state of APA cis-keto tautomer (conformer X) is calculated to be 4.3 kcal/mol (Table I) higher than APA enol tautomer. 21 Therefore, H-bond interaction with HFIP decreases the energy difference in both tautomers energies to the values allowing the existence of the equilibrium for APA in the ground state. On the contrary, the calculations for SAA (with the same basis sets) predict a higher 7.3 kcal/mol energy difference in HEX (Table S2), and the interaction with HFIP is not enough to populate cis-keto tautomer at room temperature.…”

Section: B Steady State Absorption and Emissionmentioning

confidence: 94%

“…21. The solvents used were the same as in our earlier paper, 23 their abbreviations and solvatochromic parameters are given in Table S1 (supplementary material 40 ).…”

Section: Methodsmentioning

confidence: 99%

“…Conformers I and II were observed in argon matrix in the ground state. 21 As regards the structural difference of these two conformers in APA, conformer I is flat with both phenol rings being planar, whereas for conformer II such rings are bit twisted (angle CNNC = 155.5 • ). It is noticeable that for SAA the process of optimization brings about a gradual merger of conformers I and II to become one -conformer I.…”

Section: A Conformational Analysis and Theoretical Description Of Spmentioning

confidence: 99%

“…The theoretical studies by quantum mechanical and semi-empirical methods of the ground and excited states are presented in a number of papers. [15][16][17][18][19][20][21] It should be stressed that one of the main aims of the present study is to investigate the effect of the strength of intramolecular hydrogen bond on the photochromic cycle of azine derivatives of Schiff bases by comparison of the results for 2 -hydroxyacetophenone azine (APA) with those previously obtained for salicyaldehyde azine (SAA). 22 …”

Section: Introductionmentioning

confidence: 98%

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Photochromic cycle of 2′-hydroxyacetophenone azine studied by absorption and emission spectroscopy in different solvents

Filipczak

Karolczak

Lipkowski

et al. 2013

The Journal of Chemical Physics

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This paper reports on the investigations of the synthesized di-(o-hydroxyaryl ketoimine) compound by the steady state absorption and emission techniques as well as picosecond time resolved emission and femtosecond transient absorption methods in different solvents. The results of the experimental observation have been supported by the theoretical DFT and TD-DFT calculations. The theoretical data have revealed the completed influence of the environmental polarity on particular conformers of studied compound. Dependencies between the activation rate constant and polarizability function as well as Kamlet-Abbond-Taft hydrogen-bonding parameter have been obtained in different solvent. The mechanism of photodynamic changes of di-(o-hydroxyaryl ketoimine) is presented.

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Perfect Polar Alignment of Parallel Beloamphiphile Layers: Improved Structural Design Bias Realized in Ferroelectric Crystals of the Novel “Methoxyphenyl Series of Acetophenone Azines”

Bhoday,

Knotts,

Glaser

2024

Chemistry A European J

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An improved design is described for ferroelectric crystals and implemented with the “methoxyphenyl series” of acetophenone azines, (MeO−Ph, Y)‐azines with Y=F (1), Cl (2), Br (3), or I (4). The crystal structures of these azines exhibit polar stacking of parallel beloamphiphile monolayers (PBAMs). Azines 1, 3, and 4 form true racemates whereas chloroazine 2 crystallizes as a kryptoracemate. Azines 1–4 are helical because of the N−N bond conformation. In true racemates the molecules of opposite helicity (M and P) are enantiomers A(M) and A*(P) while in kryptoracemates they are diastereomers A(M) and B*(P). The stacking mode of PBAMs is influenced by halogen bonding, with 2–4 showcasing a kink due to directional interlayer halogen bonding, whereas fluoroazine 1 demonstrates ideal polar stacking by avoiding it. Notably, (MeO−Ph, Y)‐azines display a stronger bias for dipole parallel alignment, attributed to the linearity of the biphenyl moiety as compared to the phenoxy series of (PhO, Y)‐azines with their non‐linear Ph−O−Ph moiety. The crystals of 1–4 all feature planar biphenyls and this synthon facilitates their crystallization through potent triple T‐contacts and enhances their nonlinear optical (NLO) performance by increasing conjugation length and affecting favorable chromophore conformations in the solids.

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CNNC conformational isomers of 2′-hydroxyacetophenone azine: FTIR matrix isolation and DFT study

Cited by 14 publications

References 28 publications

Unsymmetrical cyrhetrenyl and ferrocenyl azines derived from 5-nitrofurane: Synthesis, structural characterization and electrochemistry

Unsymmetrical cyrhetrenyl and ferrocenyl azines derived from 5-nitrofurane: Synthesis, structural characterization and electrochemistry

Photochromic cycle of 2′-hydroxyacetophenone azine studied by absorption and emission spectroscopy in different solvents

Perfect Polar Alignment of Parallel Beloamphiphile Layers: Improved Structural Design Bias Realized in Ferroelectric Crystals of the Novel “Methoxyphenyl Series of Acetophenone Azines”

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