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Synthesis and Investigation of Electro-Optical Properties of H-Shape Dibenzofulvene Derivatives

We have synthetized two classes of dibenzofulvene-arylamino derivatives with an H-shape design, for a total of six different molecules. The molecular structures consist of two D-A-D units connected by a thiophene or bitiophene bridge, using diarylamino substituents as donor groups anchored to the 2,...

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Autores principales: Giangregorio, Maria Michela, Gambino, Salvatore, Fabiano, Eduardo, Leoncini, Mauro, Cardone, Antonio, Corrente, Giuseppina Anna, Beneduci, Amerigo, Accorsi, Gianluca, Gigli, Giuseppe, Losurdo, Maria, Termine, Roberto, Capodilupo, Agostina-Lina
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2022
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8838082/
https://www.ncbi.nlm.nih.gov/pubmed/35164355
http://dx.doi.org/10.3390/molecules27031091
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author Giangregorio, Maria Michela
Gambino, Salvatore
Fabiano, Eduardo
Leoncini, Mauro
Cardone, Antonio
Corrente, Giuseppina Anna
Beneduci, Amerigo
Accorsi, Gianluca
Gigli, Giuseppe
Losurdo, Maria
Termine, Roberto
Capodilupo, Agostina-Lina
author_facet Giangregorio, Maria Michela
Gambino, Salvatore
Fabiano, Eduardo
Leoncini, Mauro
Cardone, Antonio
Corrente, Giuseppina Anna
Beneduci, Amerigo
Accorsi, Gianluca
Gigli, Giuseppe
Losurdo, Maria
Termine, Roberto
Capodilupo, Agostina-Lina
author_sort Giangregorio, Maria Michela
collection PubMed
description We have synthetized two classes of dibenzofulvene-arylamino derivatives with an H-shape design, for a total of six different molecules. The molecular structures consist of two D-A-D units connected by a thiophene or bitiophene bridge, using diarylamino substituents as donor groups anchored to the 2,7- (Group A) and 3,6- (Group B) positions of the dibenzofulvene backbone. The donor units and the thiophene or bithiophene bridges were used as chemico-structural tools to modulate electro-optical and morphological-electrical properties. A combination of experiments, such as absorption measurements (UV-Vis spectroscopy), cyclic voltammetry, ellipsometry, Raman, atomic force microscopy, TD-DFT calculation and hole-mobility measurements, were carried out on the synthesized small organic molecules to investigate the differences between the two classes and therefore understand the relevance of the molecular design of the various properties. We found that the anchoring position on dibenzofulvene plays a crucial key for fine-tuning the optical, structural, and morphological properties of molecules. In particular, molecules with substituents in 2,7 positions (Group A) showed a lower structural disorder, a larger molecular planarity, and a lower roughness.
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spelling pubmed-88380822022-02-13 Synthesis and Investigation of Electro-Optical Properties of H-Shape Dibenzofulvene Derivatives Giangregorio, Maria Michela Gambino, Salvatore Fabiano, Eduardo Leoncini, Mauro Cardone, Antonio Corrente, Giuseppina Anna Beneduci, Amerigo Accorsi, Gianluca Gigli, Giuseppe Losurdo, Maria Termine, Roberto Capodilupo, Agostina-Lina Molecules Article We have synthetized two classes of dibenzofulvene-arylamino derivatives with an H-shape design, for a total of six different molecules. The molecular structures consist of two D-A-D units connected by a thiophene or bitiophene bridge, using diarylamino substituents as donor groups anchored to the 2,7- (Group A) and 3,6- (Group B) positions of the dibenzofulvene backbone. The donor units and the thiophene or bithiophene bridges were used as chemico-structural tools to modulate electro-optical and morphological-electrical properties. A combination of experiments, such as absorption measurements (UV-Vis spectroscopy), cyclic voltammetry, ellipsometry, Raman, atomic force microscopy, TD-DFT calculation and hole-mobility measurements, were carried out on the synthesized small organic molecules to investigate the differences between the two classes and therefore understand the relevance of the molecular design of the various properties. We found that the anchoring position on dibenzofulvene plays a crucial key for fine-tuning the optical, structural, and morphological properties of molecules. In particular, molecules with substituents in 2,7 positions (Group A) showed a lower structural disorder, a larger molecular planarity, and a lower roughness. MDPI 2022-02-06 /pmc/articles/PMC8838082/ /pubmed/35164355 http://dx.doi.org/10.3390/molecules27031091 Text en © 2022 by the authors. https://creativecommons.org/licenses/by/4.0/Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Giangregorio, Maria Michela
Gambino, Salvatore
Fabiano, Eduardo
Leoncini, Mauro
Cardone, Antonio
Corrente, Giuseppina Anna
Beneduci, Amerigo
Accorsi, Gianluca
Gigli, Giuseppe
Losurdo, Maria
Termine, Roberto
Capodilupo, Agostina-Lina
Synthesis and Investigation of Electro-Optical Properties of H-Shape Dibenzofulvene Derivatives
title Synthesis and Investigation of Electro-Optical Properties of H-Shape Dibenzofulvene Derivatives
title_full Synthesis and Investigation of Electro-Optical Properties of H-Shape Dibenzofulvene Derivatives
title_fullStr Synthesis and Investigation of Electro-Optical Properties of H-Shape Dibenzofulvene Derivatives
title_full_unstemmed Synthesis and Investigation of Electro-Optical Properties of H-Shape Dibenzofulvene Derivatives
title_short Synthesis and Investigation of Electro-Optical Properties of H-Shape Dibenzofulvene Derivatives
title_sort synthesis and investigation of electro-optical properties of h-shape dibenzofulvene derivatives
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8838082/
https://www.ncbi.nlm.nih.gov/pubmed/35164355
http://dx.doi.org/10.3390/molecules27031091
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