Helicenes from diarylmaleimides

Harald Bock; Daniel Subervie; Pierre Mathey; Anirban Pradhan; Parantap Sarkar; Pierre Dechambenoit; Elizabeth A. Hillard; Fabien Durola

doi:10.1021/ol500154k

Helicenes from diarylmaleimides

Harald Bock, Daniel Subervie, Pierre Mathey, Anirban Pradhan, Parantap Sarkar, Pierre Dechambenoit, Elizabeth A. Hillard, Fabien Durola

Research output: Contribution to journal › Article › peer-review

37 Citations (Scopus)

Abstract

Perkin condensations of arylglyoxylic acids with arylacetic acids, followed by the addition of alkylamine, yield diarylmaleimides in a one-pot procedure. The arylglyoxylic acids are obtained by arene acylation with ClCOCO ₂Et and reduced with NaI and hypophosphorous acid to the arylacetic acids. With 2,7-di-tert-butyl-pyren-4-yl or chrysen-6-yl as the aryl, photocyclodehydrogenation of the diarylmaleimides yields substituted helicenes which can be reduced to stable anions. The helicenes combine bathochromically shifted absorption with hypsochromically shifted fluorescence with respect to their precursors.

Original language	English
Pages (from-to)	1546-1549
Number of pages	4
Journal	Organic letters
Volume	16
Issue number	6
DOIs	https://doi.org/10.1021/ol500154k
Publication status	Published - 2014 Mar 21

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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abstract = "Perkin condensations of arylglyoxylic acids with arylacetic acids, followed by the addition of alkylamine, yield diarylmaleimides in a one-pot procedure. The arylglyoxylic acids are obtained by arene acylation with ClCOCO 2Et and reduced with NaI and hypophosphorous acid to the arylacetic acids. With 2,7-di-tert-butyl-pyren-4-yl or chrysen-6-yl as the aryl, photocyclodehydrogenation of the diarylmaleimides yields substituted helicenes which can be reduced to stable anions. The helicenes combine bathochromically shifted absorption with hypsochromically shifted fluorescence with respect to their precursors.",

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T1 - Helicenes from diarylmaleimides

AU - Bock, Harald

AU - Subervie, Daniel

AU - Mathey, Pierre

AU - Pradhan, Anirban

AU - Sarkar, Parantap

AU - Dechambenoit, Pierre

AU - Hillard, Elizabeth A.

AU - Durola, Fabien

PY - 2014/3/21

Y1 - 2014/3/21

N2 - Perkin condensations of arylglyoxylic acids with arylacetic acids, followed by the addition of alkylamine, yield diarylmaleimides in a one-pot procedure. The arylglyoxylic acids are obtained by arene acylation with ClCOCO 2Et and reduced with NaI and hypophosphorous acid to the arylacetic acids. With 2,7-di-tert-butyl-pyren-4-yl or chrysen-6-yl as the aryl, photocyclodehydrogenation of the diarylmaleimides yields substituted helicenes which can be reduced to stable anions. The helicenes combine bathochromically shifted absorption with hypsochromically shifted fluorescence with respect to their precursors.

AB - Perkin condensations of arylglyoxylic acids with arylacetic acids, followed by the addition of alkylamine, yield diarylmaleimides in a one-pot procedure. The arylglyoxylic acids are obtained by arene acylation with ClCOCO 2Et and reduced with NaI and hypophosphorous acid to the arylacetic acids. With 2,7-di-tert-butyl-pyren-4-yl or chrysen-6-yl as the aryl, photocyclodehydrogenation of the diarylmaleimides yields substituted helicenes which can be reduced to stable anions. The helicenes combine bathochromically shifted absorption with hypsochromically shifted fluorescence with respect to their precursors.

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Helicenes from diarylmaleimides

Abstract

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