Straightforward, Sustainable and Scalable Access to 3,4-Perylenedicarboxylic Monoanhydride

08 March 2024, Version 1
This content is a preprint and has not undergone peer review at the time of posting.

Abstract

Perylene dyes are a cornerstone of modern research and technology in fields rang- ing from printed (opto)eletronics to bioimaging. Most known compounds are bisimide derivatives prepared from perylenetetracarboxylic dianhydride (PTCDA), essentially a chemical commodity. On the contrary, there are comparatively fewer reports on perilenedicarboxylic monoimide derivatives not due to lack of performance but due to the challenging access to the key intermediate 3,4-perylenedicarboxylic monoanhy- dride (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.

Keywords

perylene monoanhydride
perylene dyes
scalable synthesis
green chemistry

Supplementary materials

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Supporting information
Description
Materials and methods for the preparation of PDCMA, 11 and 10. Details on calculation of green metrics used and of the selected cost model. Details on the calculations of cost and E-factor according to literature data. Details on the calculation of E-Factor and cost according to the procedure described in this paper. TGA and UV/Vis characterization of PDCMA. Copies of 1H and 13C NMR spectra.
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