Alkylated benzodithienoquinolizinium salts as possible non-fullerene organic n-type semiconductors: An experimental and theoretical study

Andrés Aracena; Marcos Caroli Rezende; Macarena García; Karina Muñoz-Becerra; Kerry Wrighton-Araneda; Cristian Valdebenito; Freddy Celis; Octavio Vásquez

doi:10.3390/ma14216239

Alkylated benzodithienoquinolizinium salts as possible non-fullerene organic n-type semiconductors: An experimental and theoretical study

Andrés Aracena, Marcos Caroli Rezende, Macarena García, Karina Muñoz-Becerra, Kerry Wrighton-Araneda, Cristian Valdebenito, Freddy Celis, Octavio Vásquez

Facultad de Medicina Veterinaria y Agronomía

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2 Scopus citations

Abstract

Three photobicyclized benzodithienoquinolizinium tetrafluoroborates (BPDTQBF4) were prepared and evaluated by UV–Vis and fluorescence spectral, electrochemical analysis, and by theoretical calculations as possible organic n-type semiconductors. Evaluation and comparison of their LUMO levels, HOMO-LUMO energy gaps as monomeric and π-stacked dimers with those of other materials, suggest their potential as organic n-type semiconductors. Calculations of their relative charge carrier mobilities confirmed this potential for one derivative with a long (C-14) alkyl chain appended to the polycyclic planar π-system.

Original language	English
Article number	6239
Journal	Materials
Volume	14
Issue number	21
DOIs	https://doi.org/10.3390/ma14216239
State	Published - 1 Nov 2021

Keywords

Benzodithienoquinolizinium cations
Organic semiconductors
Photocyclization of N-aryl pyridinium salts
π-stacked assemblies

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10.3390/ma14216239

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title = "Alkylated benzodithienoquinolizinium salts as possible non-fullerene organic n-type semiconductors: An experimental and theoretical study",

abstract = "Three photobicyclized benzodithienoquinolizinium tetrafluoroborates (BPDTQBF4) were prepared and evaluated by UV–Vis and fluorescence spectral, electrochemical analysis, and by theoretical calculations as possible organic n-type semiconductors. Evaluation and comparison of their LUMO levels, HOMO-LUMO energy gaps as monomeric and π-stacked dimers with those of other materials, suggest their potential as organic n-type semiconductors. Calculations of their relative charge carrier mobilities confirmed this potential for one derivative with a long (C-14) alkyl chain appended to the polycyclic planar π-system.",

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T2 - An experimental and theoretical study

AU - Aracena, Andrés

AU - Rezende, Marcos Caroli

AU - García, Macarena

AU - Muñoz-Becerra, Karina

AU - Wrighton-Araneda, Kerry

AU - Valdebenito, Cristian

AU - Celis, Freddy

AU - Vásquez, Octavio

PY - 2021/11/1

Y1 - 2021/11/1

N2 - Three photobicyclized benzodithienoquinolizinium tetrafluoroborates (BPDTQBF4) were prepared and evaluated by UV–Vis and fluorescence spectral, electrochemical analysis, and by theoretical calculations as possible organic n-type semiconductors. Evaluation and comparison of their LUMO levels, HOMO-LUMO energy gaps as monomeric and π-stacked dimers with those of other materials, suggest their potential as organic n-type semiconductors. Calculations of their relative charge carrier mobilities confirmed this potential for one derivative with a long (C-14) alkyl chain appended to the polycyclic planar π-system.

AB - Three photobicyclized benzodithienoquinolizinium tetrafluoroborates (BPDTQBF4) were prepared and evaluated by UV–Vis and fluorescence spectral, electrochemical analysis, and by theoretical calculations as possible organic n-type semiconductors. Evaluation and comparison of their LUMO levels, HOMO-LUMO energy gaps as monomeric and π-stacked dimers with those of other materials, suggest their potential as organic n-type semiconductors. Calculations of their relative charge carrier mobilities confirmed this potential for one derivative with a long (C-14) alkyl chain appended to the polycyclic planar π-system.

KW - Benzodithienoquinolizinium cations

KW - Organic semiconductors

KW - Photocyclization of N-aryl pyridinium salts

KW - π-stacked assemblies

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U2 - 10.3390/ma14216239

DO - 10.3390/ma14216239

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ER -

Alkylated benzodithienoquinolizinium salts as possible non-fullerene organic n-type semiconductors: An experimental and theoretical study

Abstract

Keywords

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