resumo
The design and synthesis of strained aromatics provide an additional insight into the relationship between structure and properties. In the last years, several approaches to twist pyrene-fused azaacenes have been developed that allow to introduce twists of different sizes. Herein, we describe the synthesis of a new set of twisted dibenzotetraazahexacenes constituted by fused pyrene and quinoxaline residues that have been distorted by introducing increasingly larger substituents on the quinoxaline residues. Their twisted structure has been demonstrated by single-crystal X-ray diffraction. Furthermore, absorption, fluorescence, electrochemical and theoretical studies shine light on the effects of the substituents and twists on the optoelectronic and redox properties. A series of twisted pyrene-fused twistacenes has been synthesized that allowed the investigation of the effects of different sterically-demanding groups on their structure and properties.image
palavras-chave
CHIRALITY; ACENES
categoria
Chemistry
autores
Mateos-Martín, J; Dhbaibi, K; Melle-Franco, M; Mateo-Alonso, A
nossos autores
Manuel Melle-Franco
Investigador PrincipalProjectos
Projeto de Investigação Exploratória: Manuel Melle (IF Manuel Melle)
CICECO - Aveiro Institute of Materials (UIDB/50011/2020)
CICECO - Aveiro Institute of Materials (UIDP/50011/2020)
Associated Laboratory CICECO-Aveiro Institute of Materials (LA/P/0006/2020)
agradecimentos
This work was carried out with support from the Basque Science Foundation for Science (Ikerbasque), POLYMAT, the University of the Basque Country, Diputacion de Guipuzcoa, Gobierno Vasco (PIBA_2022_1_0031 and BERC programme) and Gobierno de Espana (Projects PID2021-124484OB-I00 and CEX2020-001067-M financed by MCIN/AEI/10.13039/501100011033). Project (PCI2022-132921) funded by the Agencia Estatal de Investigacion through the PCI 2022 and M-ERA.NET 2021 calls. This project has received funding from the European Research Council (ERC) under the European Union's Horizon2020 research and innovation programme (Grant Agreement No. 722951). This work was funded by the European Union under the Horizon Europe grant 101046231. Technical and human support provided by SGIker of UPV/EHU and European funding (ERDF and c) is acknowledged. In addition, support through the project IF/00894/2015, the advanced computing project 2021.09622. CPCA granting access to the Navigator cluster at LCA-UC, and within the scope of the project CICECO-Aveiro Institute of Materials, UIDB/50011/2020, UIDP/50011/2020 & LA/P/0006/2020, financed by national funds through the FCT/MEC (PIDDAC) is gratefully acknowledged.