Mono- and di-substituted pyrene-based donor-π-acceptor systems with phenyl and thienyl π-conjugating bridges

Nan, Monica Irina; Lakatos, Eszter; Giurgi, Gavril-Ionel; Szolga, Loránt András; Pò, Riccardo; Terec, Anamaria; Jungsuttiwong, Siriporn; Grosu, Ion; Roncali, Jean

doi:10.1016/j.dyepig.2020.108527

Cited by 32 publications

(31 citation statements)

References 32 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Table 1 shows that the parent molecule has calculated values of HOMO/LUMO at 2.557/À5.767 eV, which is in close accordance with the experimentally determined HOMO/LUMO values of À2.780/À5.730 eV. 40 This good agreement points out that the implemented DFT computations, i.e., M06 level with 6-31G(d, p) basis set is apt to investigate MCPTD1-MCPTD8. The reference compound (MCPTR) has a larger band gap value, i.e., 3.210 eV, than all of its derivatives.…”

Section: Electronic Structuresupporting

confidence: 82%

“…1 In the recent study, we used the original compound named methyl (E)-2-cyano-3-(5-(pyren-1yl)thiophen-2-yl)acrylate with D-p-A conguration, which is abbreviated as MCPTR. 19 The designed series of NLO-based compounds were developed by structural modeling of MCPTR by modication of the acceptor. First of all, we designed MCPTD1 from the parent molecule (MCPTR) by keeping the D-p part preserved, as taken from the parent molecule (MCPTR), and introducing a pyren-1-yl moiety as a donor and thiophen as p-spacer units before the acceptor.…”

Section: Resultsmentioning

confidence: 99%

“…The HOMO is located on such orbital having an electron-donating tendency, while the LUMO is considered as the orbital that is partially lled, having an electron-accepting tendency. 19 The decreased HOMO-LUMO band gap, which can be highly polarizable, can elevate the NLO response. 37,39 FMO analysis of MCPTR and MCPTD1-MCPTD8 was carried out, and the results are collected in Table 1.…”

Section: Electronic Structurementioning

confidence: 99%

“…Its solid structure is based upon the two-dimensional geometry having a strong tendency toward p assembly, and the great variation in functional groups onto graphite, fullerenes 15,16 and graphene 17,18 make it attractive towards NLO applications. 19 We have designed an appropriate donor-p-spacer-acceptor of pyrene-based molecules containing an acceptor (cyano vinyl ester) allied to pyrene centered by thienyl or phenyl conjugating linkers. 19,20 These structural variations give promising NLO results towards pi spacer end capped donor-acceptor frameworks.…”

Section: Introductionmentioning

confidence: 99%

“…19 We have designed an appropriate donor-p-spacer-acceptor of pyrene-based molecules containing an acceptor (cyano vinyl ester) allied to pyrene centered by thienyl or phenyl conjugating linkers. 19,20 These structural variations give promising NLO results towards pi spacer end capped donor-acceptor frameworks. [21][22][23][24] These compounds may receive signicant interest in their optoelectronic applications in the zone of photonic gadgets, sensors and optical exchanging.…”

Section: Introductionmentioning

confidence: 99%

See 4 more Smart Citations

Structural parameter-modulated nonlinear optical amplitude of acceptor–π–D–π–donor-configured pyrene derivatives: a DFT approach

et al. 2021

View full text Add to dashboard Cite

show abstract

Section: Electronic Structuresupporting

confidence: 82%

Section: Resultsmentioning

confidence: 99%

Section: Electronic Structurementioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 3 more Smart Citations

Structural parameter-modulated nonlinear optical amplitude of acceptor–π–D–π–donor-configured pyrene derivatives: a DFT approach

et al. 2021

View full text Add to dashboard Cite

show abstract

In Situ Electrochemical Investigations of Inherently Chiral 2,2′‐Biindole Architectures with Oligothiophene Terminals

et al. 2021

View full text Add to dashboard Cite

The synthesis and characterization of three new inherently chiral N,N′‐dipropyl‐3,3′‐diheteroaryl‐2,2′‐biindole monomers, nicknamed Ind2T4, Ind2T6 and Ind2Ph2T4, which differ in the number of thiophenes as terminals, are reported. In addition to a full monomer characterization, stable electroactive oligomeric films were obtained by electro‐oxidation upon cycling to potentials which activate the thiophene terminals. Cyclic voltammetry, UV‐Vis‐NIR spectroelectrochemistry and in situ conductance measurements show that oligomeric films of Ind2T6 present the best stability and electrochromic switching performance. Enantioselective tests with a chiral ferrocene amine clearly show the potential as chiral selectors for analytical and sensing purposes.

show abstract

Modulating the Enantiodiscrimination Features of Inherently Chiral Selectors by Molecular Design: A HPLC and Voltammetry Study Case with Atropisomeric 2,2’‐Biindole‐Based Monomers and Oligomer Films

Scapinello

Grecchi

Rossi

et al. 2021

Chemistry A European J

View full text Add to dashboard Cite

A family of inherently chiral electroactive selectors based on the 2,2'-biindole atropisomeric scaffold, of easy synthesis and modulable functional properties, is studied in cascade in two enantioselection contexts. They are at first investigated as probes in enantioselective HPLC, studying molecular structure and temperature effects, and achieving very efficient semipreparative enantioseparation. The enantiomers thus obtained, of remarkable chiroptical features (optical rotation as well as circular dichroism), are successfully applied as selectors in chiral voltammetry in different media for discrimination of the enantiomers of chiral electroactive probes, either by conversion into enantiopure electroactive electrode surfaces by electrooligomerization on glassy carbon substrate (the two monomers with shorter alkyl chains), or as chiral additive in achiral ionic liquid (the monomer with longest alkyl chains). Discrimination is conveniently and reproducibly achieved in terms of significant potential differences for the two enantiomers, specularly inverting either probe or selector configuration. In one case successful discrimination is also observed with the two probe enantiomers concurrently present, either as racemate or with enantiomeric excesses, neatly accounted for by the peak current ratios.

show abstract

Mono- and di-substituted pyrene-based donor-π-acceptor systems with phenyl and thienyl π-conjugating bridges

Cited by 32 publications

References 32 publications

Structural parameter-modulated nonlinear optical amplitude of acceptor–π–D–π–donor-configured pyrene derivatives: a DFT approach

Structural parameter-modulated nonlinear optical amplitude of acceptor–π–D–π–donor-configured pyrene derivatives: a DFT approach

In Situ Electrochemical Investigations of Inherently Chiral 2,2′‐Biindole Architectures with Oligothiophene Terminals

Modulating the Enantiodiscrimination Features of Inherently Chiral Selectors by Molecular Design: A HPLC and Voltammetry Study Case with Atropisomeric 2,2’‐Biindole‐Based Monomers and Oligomer Films

Contact Info

Product

Resources

About