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 | |
| Publication status | Published - 2004 Jan 9 |
| Externally published | Yes |
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ASJC Scopus subject areas
- Organic Chemistry
Cite this
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
}
TY - JOUR
T1 - Avenues into the Synthesis of Illusive Poly(m-phenylene-alt-squaraine)s
T2 - Polycondensation of m-Phenylenediamines with Squaric Acid Intercepted by Intermediate Semisquaraines of Exceptionally Low Reactivity
AU - Balbo Block, Marco A.
AU - Khan, Anzar
AU - Hecht, Stefan
PY - 2004/1/9
Y1 - 2004/1/9
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.
UR - http://www.scopus.com/inward/record.url?scp=0347991830&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=0347991830&partnerID=8YFLogxK
U2 - 10.1021/jo035399z
DO - 10.1021/jo035399z
M3 - Article
VL - 69
SP - 184
EP - 187
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
SN - 0022-3263
IS - 1
ER -