Symmetrical N-acylsubstituted dihydrazones containing bithiophene core — Photophysical, electrochemical and thermal characterization

Jarczyk-Jedryka, Anna; Filapek, Michał; Małecki, Jan Grzegorz; Kula, Sławomir; Janeczek, Henryk; Boharewicz, Bartosz; Iwan, Agnieszka; Schab‐Balcerzak, Ewa

doi:10.1016/j.saa.2016.01.034

Cited by 6 publications

(11 citation statements)

References 66 publications

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“…Highest occupied molecular orbitals (HOMO), lowest unoccupied molecular orbitals (LUMO), and the energy gap (E G ) of all the molecules are provided in Figure . Jarczyk‐Jedryka and coworkers have optimized BTS and BTO using the PCM solvation model with dichloromethane as a solvation medium . The HOMO and LUMO values reported by Jarczyk‐Jedryka are identical with the results reported herein; however, the slight energy differences observed arise due to the selection of basis set and the solvent medium considered.…”

Section: Resultssupporting

confidence: 67%

“…The contribution from HOMO − 1 and LUMO + 1 orbitals is quite insignificant, and hence the discussion herein is solely restricted to HOMO and LUMO orbitals. The electronic distribution of HOMO and LUMO is mainly distributed over the bithiophene core and a portion of the hydrazide group excluding the heterocyclic ring on either side as observed . The nature of electronic transition arising from HOMO and LUMO is of π‐π* type, and one can conclude that the transitions occurring within the system are mainly supported by the bithiophene core.…”

Section: Resultsmentioning

confidence: 58%

“…The nature of electronic transition arising from HOMO and LUMO is of π‐π* type, and one can conclude that the transitions occurring within the system are mainly supported by the bithiophene core. The energy gap of BTS , BTO, and BTN is nearly the same owing to their structure possessing similar compositions . Electronic cloud surrounding (N―H) proton donor at the LUMO level shrinks to a larger extent in comparison to that observed at the HOMO level, and such changes were not observed for the proton acceptor moiety (C═O) .…”

Section: Resultsmentioning

confidence: 96%

“…Jedryka‐Jarczyk and co‐workers have meticulously designed and synthesized Schiff's base symmetrical N‐acylsubstituted dihydrazones containing bithiophene core to look into practical solar cell applications . Among the molecules designed, bithiophene coupled with furoic hydrazide turns out to be the best competitor as an active solar energy harvester.…”

Section: Introductionmentioning

confidence: 99%

“…We would like to present further a few of the experimental results that were not done and reported earlier by Jedryka‐Jarczyk et al, to provide necessary support for the theoretical validation. Jarczyk‐Jedryka reported TBTH and FBTH (herein referred to as BTS and BTO, respectively) . BTN varies from NBTH in possessing a hydrazide unit at position meta to the pyridine ring nitrogen.…”

Section: Introductionmentioning

confidence: 99%

See 4 more Smart Citations

Exploring the possibilities of double proton transfer in hydrazides: A theoretical approach

Mohan

Satyanarayan

Trivedi

2019

J of Physical Organic Chem

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Hydrazides are known to exhibit keto‐enol tautomerism upon photoexcitation. Theoretical aspects uncovering excited state intramolecular proton transfer (ESIPT) of N‐acylsubstituted hydrazides with bithiophene core have been investigated. Geometrical aspects of the system are expected to undergo double proton translocation at its excited state. However, potential energy surface study for all the molecules reveals an impossible concurrent double proton translocation and to a greater extent dubious step‐wise double proton translocation in the system. Potential energy scans reveal molecules possessing a lower forward barrier at its excited state in comparison with their ground state suggestive of possible excited state single proton transfer. Geometrical attributes and spectral analysis suggest the strengthening of intramolecular hydrogen bond (N―H▪▪▪O) at its excited state, favoring single proton translocation. Theoretical estimation of electronic energy transition for all the conformers yields good correlation with the experimental figures with an energy overestimation <0.17 eV.

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Section: Resultssupporting

confidence: 67%

Section: Resultsmentioning

confidence: 58%

Section: Resultsmentioning

confidence: 96%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 3 more Smart Citations

Exploring the possibilities of double proton transfer in hydrazides: A theoretical approach

Mohan

Satyanarayan

Trivedi

2019

J of Physical Organic Chem

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Preparation and Characterization of poly(Azomethines) Containing Ether and Methylene Bridges: Photophysical, Electrochemical, Conductivity and Thermal Properties

Kaya

Yilmaz

2016

J Fluoresc

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In this paper, a series of polyazomethines (PAZs) were prepared using dihydroxy substituted Schiff bases and 1,4-diiodobenzene. Also, different group effect such as methylene carbon and etheric oxygen bridges on photophysical, electrochemical, conductivity and thermal properties were clarified. The new polymeric materials structures were confirmed by means of H-NMR, FT-IR and UV-vis measurements. The molecular weight distributions of polymers were determined with gel permeation chromatography (GPC) measurements. Photophysical behaviors of polymers were explored by UV-vis absorption and fluorescence measurements. TGA-DTA and DSC techniques have been used for the thermal characterization of the PAZs. Thermal data and fluorescence measurements showed that etheric oxygen bridge containing polymers have a bit higher char and emission intensity than the methylene carbon bridge carrying polymers. According to TG analysis, T values of P-2MPDP, P-2-OPDP, P-4-MPDP and P-4-OPDP were found as 210, 250, 249 and 233 °C, respectively. The HOMO-LUMO energy levels, electrochemical (E' ) and optical (E ) band gaps were calculated from cyclic voltammetry (CV) and UV-vis measurements, respectively. The electrochemical (E ') band gaps values of P-2MPDP, P-2-OPDP, P-4-MPDP and P-4-OPDP were calculated as 2.68, 2.32, 2.34 and 2.07, respectively. Additionally, four-point probe technique was used to measure solid state electrical conductivities of both doped and undoped states of the PAZs.

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Physical–chemical characterization of N-acylhydrazone derivative chitosan films using spectroscopic and thermoanalytical techniques

Wanderley

Melo

Silva

et al. 2019

J Therm Anal Calorim

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Symmetrical N-acylsubstituted dihydrazones containing bithiophene core — Photophysical, electrochemical and thermal characterization

Cited by 6 publications

References 66 publications

Exploring the possibilities of double proton transfer in hydrazides: A theoretical approach

Exploring the possibilities of double proton transfer in hydrazides: A theoretical approach

Preparation and Characterization of poly(Azomethines) Containing Ether and Methylene Bridges: Photophysical, Electrochemical, Conductivity and Thermal Properties

Physical–chemical characterization of N-acylhydrazone derivative chitosan films using spectroscopic and thermoanalytical techniques

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