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 journalArticle

15 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 languageEnglish
Pages (from-to)184-187
Number of pages4
JournalJournal of Organic Chemistry
Volume69
Issue number1
DOIs
Publication statusPublished - 2004 Jan 9
Externally publishedYes

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Hydrogen Bonding
Polycondensation
Hydrogen
Hydrogen bonds
Sensors
3-phenylenediamine
squaric acid
squaraine

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

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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.",
author = "{Balbo Block}, {Marco A.} and Anzar Khan and Stefan Hecht",
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AU - Hecht, Stefan

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N2 - 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.

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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