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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 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: 25 Oct 2019 02:14
URI: http://orca.cf.ac.uk/id/eprint/116697

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