Tailored synthesis of N-substituted peri-Xanthenoxanthene Diimide (PXXDI) and Monoimide (PXXMI) Scaffolds

Sciutto, Andrea, Berezin, Andrey, Lo Cicero, Matteo, Miletic, Tanja, Stopin, Antoine and Bonifazi, Davide ORCID: https://orcid.org/0000-0001-5717-0121 2018. Tailored synthesis of N-substituted peri-Xanthenoxanthene Diimide (PXXDI) and Monoimide (PXXMI) Scaffolds. Journal of Organic Chemistry 83 (22) , pp. 13787-13798. 10.1021/acs.joc.8b02076

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Abstract

The tailored synthesis of homo (A2) and hetero (AB) N-substituted peri-xanthenoxanthene diimides (PXXDIs) and peri-functionalized PXX monoimides (PXXMIs) from 3-hydroxy naphthalic anhydride is described. As A2-type PXXDIs could be synthesized in one step, AB-type PXXDIs and PXXMIs were prepared through a modular approach capitalizing on sequential Suzuki coupling, imidation, and Pummerer reactions with very high yields. In view of their potential applications as organic semiconductors, self-organization studies were performed through liquid deposition on surfaces, depicting the formation of islands, needles, and rods.

Item Type:	Article
Date Type:	Publication
Status:	Published
Schools:	Chemistry
Publisher:	American Chemical Society
ISSN:	0022-3263
Funders:	MSCA-ITN ETN network �PHOTOTRAIN�, the MSCA-RISE project �INFUSION�
Date of First Compliant Deposit:	13 November 2018
Date of Acceptance:	26 October 2018
Last Modified:	14 Apr 2024 17:27
URI:	https://orca.cardiff.ac.uk/id/eprint/116697

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