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Twisted One-Dimensional Charge Transfer and Related Y-Shaped Chromophores with a 4H-Pyranylidene Donor: Synthesis and Optical Properties.


ABSTRACT: Three series of push-pull derivatives bearing 4H-pyranylidene as electron donor group and a variety of acceptors were designed. On one hand, one-dimensional chromophores with a thiophene ring (series 1H) or 5-dimethylaminothiophene moiety (series 1N) as an auxiliary donor, non-coplanar with the π-conjugated system, were synthesized. On the other hand, related two-dimensional (2D) Y-shaped chromophores (series 2) were also prepared to compare how the diverse architectures affect the electrochemical, linear, and second-order nonlinear optical (NLO) properties. The presence of the 5-dimethylaminothiophene moiety in the exocyclic C═C bond of the pyranylidene unit gives rise to oxidation potentials rarely low, and the protonation (with an excess of trifluoroacetic acid) of its derivatives results in the apparition of a new blue-shifted band in the UV-visible spectra. The analysis of the properties of derivatives with and without the additional thiophene ring shows that this auxiliary donor leads to a higher NLO response, accompanied by an enhanced transparency. Y-shaped chromophores of series 2 present a blue-shifted absorption, higher molar extinction coefficients, and higher Eox values compared to their linear twisted counterparts. As concerns NLO properties, 2D Y-shaped architecture gives rise to somewhat lower μβ values (except for thiobarbiturate derivatives).

SUBMITTER: Tejeda-Orusco V 

PROVIDER: S-EPMC9161450 | biostudies-literature | 2021 Feb

REPOSITORIES: biostudies-literature

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Twisted One-Dimensional Charge Transfer and Related Y-Shaped Chromophores with a 4<i>H</i>-Pyranylidene Donor: Synthesis and Optical Properties.

Tejeda-Orusco Víctor V   Andreu Raquel R   Orduna Jesús J   Villacampa Belén B   Franco Santiago S   Civera Alba A  

The Journal of organic chemistry 20210202 4


Three series of push-pull derivatives bearing 4<i>H</i>-pyranylidene as electron donor group and a variety of acceptors were designed. On one hand, one-dimensional chromophores with a thiophene ring (series <b>1H</b>) or 5-dimethylaminothiophene moiety (series <b>1N</b>) as an auxiliary donor, non-coplanar with the π-conjugated system, were synthesized. On the other hand, related two-dimensional (2D) Y-shaped chromophores (series <b>2</b>) were also prepared to compare how the diverse architectu  ...[more]

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