Perylene dyes are a cornerstone of modern research and technology in fields ranging from printed (opto)electronics to bioimaging. Most known compounds are bisimide derivatives prepared from perylenetetracarboxylic dianhydride (PTCDA), which is essentially a chemical commodity. On the contrary, there are comparatively fewer reports on perylenedicarboxylic monoimide derivatives not due to lack of performance but due to the challenging access to the key intermediate 3,4-perylenedicarboxylic monoanhydride (PDCMA). As we detail, reported synthetic pathways are both costly, resource intensive, and associated with extremely poor green metrics. We show a new two-step straightforward, sustainable, efficient, and organic solvent-free preparation of PDCMA based on a combination of solventless and in-water reactions.
Zucchi, A., Mattiello, S., Sassi, M., Beverina, L. (2024). Straightforward, Sustainable, and Scalable Access to 3,4-Perylenedicarboxylic Monoanhydride. ACS SUSTAINABLE CHEMISTRY & ENGINEERING, 12(22), 8533-8540 [10.1021/acssuschemeng.4c02041].
Straightforward, Sustainable, and Scalable Access to 3,4-Perylenedicarboxylic Monoanhydride
Zucchi A.Primo
;Mattiello S.;Sassi M.
;Beverina L.
2024
Abstract
Perylene dyes are a cornerstone of modern research and technology in fields ranging from printed (opto)electronics to bioimaging. Most known compounds are bisimide derivatives prepared from perylenetetracarboxylic dianhydride (PTCDA), which is essentially a chemical commodity. On the contrary, there are comparatively fewer reports on perylenedicarboxylic monoimide derivatives not due to lack of performance but due to the challenging access to the key intermediate 3,4-perylenedicarboxylic monoanhydride (PDCMA). As we detail, reported synthetic pathways are both costly, resource intensive, and associated with extremely poor green metrics. We show a new two-step straightforward, sustainable, efficient, and organic solvent-free preparation of PDCMA based on a combination of solventless and in-water reactions.File | Dimensione | Formato | |
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