Avenues into the Synthesis of Illusive Poly(m-phenylene-alt-squaraine)s: Polycondensation of m-Phenylenediamines with Squaric Acid Intercepted by Intermediate Semisquaraines of Exceptionally Low Reactivity

Marco A. Balbo Block; Anzar Khan; Stefan Hecht

doi:10.1021/jo035399z

Avenues into the Synthesis of Illusive Poly(m-phenylene-alt-squaraine)s: Polycondensation of m-Phenylenediamines with Squaric Acid Intercepted by Intermediate Semisquaraines of Exceptionally Low Reactivity

Marco A. Balbo Block, Anzar Khan, Stefan Hecht

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

16 Citations (Scopus)

Abstract

The synthesis and properties of a novel class of ortho-dialkylamino-substituted semisquaraines are described. The exceptionally low reactivity of the investigated compounds is caused by an intramolecular hydrogen bond as evidenced by experimental and computational studies. Although this constitutes the reason for our failed attempts to prepare poly(m-phenylene-alt-squaraine)s, the discovered influence of hydrogen bonding on the photophysical properties of these semisquaraines provides a promising new motif for sensor design.

Original language	English
Pages (from-to)	184-187
Number of pages	4
Journal	Journal of Organic Chemistry
Volume	69
Issue number	1
DOIs	https://doi.org/10.1021/jo035399z
Publication status	Published - 2004 Jan 9
Externally published	Yes

ASJC Scopus subject areas

Organic Chemistry

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Avenues into the Synthesis of Illusive Poly(m-phenylene-alt-squaraine)s: Polycondensation of m-Phenylenediamines with Squaric Acid Intercepted by Intermediate Semisquaraines of Exceptionally Low Reactivity. / Balbo Block, Marco A.; Khan, Anzar; Hecht, Stefan.
In: Journal of Organic Chemistry, Vol. 69, No. 1, 09.01.2004, p. 184-187.

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

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abstract = "The synthesis and properties of a novel class of ortho-dialkylamino-substituted semisquaraines are described. The exceptionally low reactivity of the investigated compounds is caused by an intramolecular hydrogen bond as evidenced by experimental and computational studies. Although this constitutes the reason for our failed attempts to prepare poly(m-phenylene-alt-squaraine)s, the discovered influence of hydrogen bonding on the photophysical properties of these semisquaraines provides a promising new motif for sensor design.",

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AB - The synthesis and properties of a novel class of ortho-dialkylamino-substituted semisquaraines are described. The exceptionally low reactivity of the investigated compounds is caused by an intramolecular hydrogen bond as evidenced by experimental and computational studies. Although this constitutes the reason for our failed attempts to prepare poly(m-phenylene-alt-squaraine)s, the discovered influence of hydrogen bonding on the photophysical properties of these semisquaraines provides a promising new motif for sensor design.

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Avenues into the Synthesis of Illusive Poly(m-phenylene-alt-squaraine)s: Polycondensation of m-Phenylenediamines with Squaric Acid Intercepted by Intermediate Semisquaraines of Exceptionally Low Reactivity

Abstract

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