Modulating Strain in Twisted Pyrene‐Fused Azaacenes

Modulating Strain in Twisted Pyrene‐Fused Azaacenes

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 sy...

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Bibliographic Details
Published in:Chemistry : a European journal Vol. 29; no. 69; pp. e202302002 - n/a
Main Authors: Mateos‐Martín, Javier, Dhbaibi, Kais, Melle‐Franco, Manuel, Mateo‐Alonso, Aurelio
Format: Journal Article
Language:English
Published: Germany Wiley Subscription Services, Inc 11-12-2023
Subjects:
@KokeLab @ManuelMelleLab and co-workers describe the synthesis of a new series of twisted pyrene-fused azaacenes @POLYMAT_BERC @ikerbasque @ehuscientia @ciceco_ua
Aromatic compounds
Chemistry
contorted aromatics
distorted aromatics
Electrochemistry
Fluorescence
Light effects
nonplanar aromatics
Optoelectronics
polycyclic aromatic hydrocarbons
Pyrene
Quinoxaline
Quinoxalines
Redox properties
Residues
Synthesis
twisted aromatics
twisted aromatics
distorted aromatics
nonplanar aromatics
contorted aromatics
polycyclic aromatic hydrocarbons
@KokeLab @ManuelMelleLab and co-workers describe the synthesis of a new series of twisted pyrene-fused azaacenes @POLYMAT_BERC @ikerbasque @ehuscientia @ciceco_ua
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Summary: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.
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ISSN:0947-6539
1521-3765
DOI:10.1002/chem.202302002