Alternative Functionalization of Hydrogen‐Bonded Diketopyrrolopyrrole Derivatives

Diketopyrrolopyrrole (DPP) derivatives with thiophene capping rings are widely used as semiconductors in organic electronics. Their optoelectronic properties can be adjusted by adding different electroactive groups or by extending the conjugation of the central core, as well as by regulating their s...

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Bibliographic Details
Published in:European journal of organic chemistry 2023-09, Vol.26 (33), p.n/a
Main Authors: Martinez, Gabriel, Ávila‐Rovelo, Nelson Ricardo, Carmona‐Vargas, Christian C., Id‐boubrik, Imrane, Ruiz‐Carretero, Amparo
Format: Article
Language:English
Subjects:
Bonding
Capping
Chemical Sciences
Conjugation
diketopyrrolopyrrole
Hydrogen
hydrogen bonding
noncovalent interactions
Optoelectronics
organic electronics
Organic semiconductors
Photovoltaic cells
Self-assembly
Solar cells
supramolecular electronics
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Summary:Diketopyrrolopyrrole (DPP) derivatives with thiophene capping rings are widely used as semiconductors in organic electronics. Their optoelectronic properties can be adjusted by adding different electroactive groups or by extending the conjugation of the central core, as well as by regulating their self‐assembly through noncovalent interactions. One effective strategy demonstrated to improve the performance and morphology of organic solar cells is incorporating hydrogen‐bonding units into DPPs. While the functionalization of the DPP lactams and the coupling of aromatic units to the thiophene rings are the most common procedures to tune the properties of such derivatives, modifying the thiophene capping units with hydrogen‐bonding groups is a challenging synthetic task. Despite this difficulty, incorporating amide‐containing substituents into the thiophene rings of single core thiophene‐capped DPP derivatives could yield exciting results, as the advantages of having hydrogen‐bonded π‐conjugated systems based on these modified DPPs have not been explored thoroughly. This work reports on an efficient method for synthesizing such derivatives. Diketopyrrolopyrrole (DPP) derivatives with thiophene capping rings are widely used as semiconductors in organic electronics. Their optoelectronic properties can be adjusted by adding different electroactive groups or by extending the conjugation of the central core, as well as by regulating their self‐assembly through noncovalent interactions. This work describes an efficient method for synthesizing such derivatives.
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.202300344