Publication result detail

Spectroscopic behavior of alloxazine-based dyes with extended aromaticity: Theory vs Experiment

CAGARDOVÁ, D; TRUKSA, J.; MICHALÍK, M; RICHTÁR, J.; WEITER, M.; KRAJČOVIČ, J.; LUKEŠ, V.

Original Title

Spectroscopic behavior of alloxazine-based dyes with extended aromaticity: Theory vs Experiment

English Title

Spectroscopic behavior of alloxazine-based dyes with extended aromaticity: Theory vs Experiment

Type

Scopus Article

Original Abstract

The chemical and electronic structure of parent (iso)alloxazine and their eight aromatic derivatives as possible candidates for dyes usage were systematically investigated by the Density Functional Theory. The effect of condensation by various (mostly benzene-like) aromatic moieties to the initial benzo[g]pteridine moiety on the energies of frontier molecular orbitals and spectroscopic properties - absorption, and emission characterization, was discussed. The spectroscopic behavior experimentally measured in alkaline dimethylsulfoxide for parent alloxazine, and its four available derivatives were compared with the theoretical predictions. In this context, the optical properties of iso-tautomers and deprotonated species were also theoretically quantified. Impact of chain modification relating to several linear and two-dimensional structure variations on electron structure and optical properties was analyzed. The correlations between theoretical estimation and experiment were proposed and could be helpful for future synthesis of novel molecules in optoelectronics or biosensing technology.

English abstract

The chemical and electronic structure of parent (iso)alloxazine and their eight aromatic derivatives as possible candidates for dyes usage were systematically investigated by the Density Functional Theory. The effect of condensation by various (mostly benzene-like) aromatic moieties to the initial benzo[g]pteridine moiety on the energies of frontier molecular orbitals and spectroscopic properties - absorption, and emission characterization, was discussed. The spectroscopic behavior experimentally measured in alkaline dimethylsulfoxide for parent alloxazine, and its four available derivatives were compared with the theoretical predictions. In this context, the optical properties of iso-tautomers and deprotonated species were also theoretically quantified. Impact of chain modification relating to several linear and two-dimensional structure variations on electron structure and optical properties was analyzed. The correlations between theoretical estimation and experiment were proposed and could be helpful for future synthesis of novel molecules in optoelectronics or biosensing technology.

Keywords

Alloxazine;Aromaticity index;Dyes;Flavins;Fluorescence;Vertical excited states

Key words in English

Alloxazine;Aromaticity index;Dyes;Flavins;Fluorescence;Vertical excited states

Authors

CAGARDOVÁ, D; TRUKSA, J.; MICHALÍK, M; RICHTÁR, J.; WEITER, M.; KRAJČOVIČ, J.; LUKEŠ, V.

RIV year

2022

Released

01.07.2021

Publisher

Elsevier B.V.

Location

Amsterdam

ISBN

0925-3467

Periodical

OPTICAL MATERIALS

Volume

117

Number

1

State

Kingdom of the Netherlands

Pages from

1

Pages to

8

Pages count

8

URL

https://www.sciencedirect.com/science/article/pii/S0925346721004067

BibTex

@article{BUT172144,
  author="CAGARDOVÁ, D and TRUKSA, J. and MICHALÍK, M and RICHTÁR, J. and WEITER, M. and KRAJČOVIČ, J. and LUKEŠ, V.",
  title="Spectroscopic behavior of alloxazine-based dyes with extended aromaticity: Theory vs Experiment",
  journal="OPTICAL MATERIALS",
  year="2021",
  volume="117",
  number="1",
  pages="1--8",
  doi="10.1016/j.optmat.2021.111205",
  issn="0925-3467",
  url="https://www.sciencedirect.com/science/article/pii/S0925346721004067"
}