Abstract
Aryl pyrimidones are pharmacologically relevant compounds whose optical properties have only been partially explored. We report the synthesis and optical characterization of a series of aryl- and diaryl-2(1H)-pyrimidones. The electronic transitions of these chromophores are modulated by the extent of conjugation between the pendant phenyl ring and the pyrimidone core as well as the presence of electron-donating auxochromes. Monoprotonation of the pyrimidone ring results in large hyperchromic and bathochromic shifts as well as switching of fluorescence making these phenyl pyrimidones of interest as sensory materials.
| Original language | English |
|---|---|
| Pages (from-to) | 4188-4191 |
| Number of pages | 4 |
| Journal | Organic Letters |
| Volume | 13 |
| Issue number | 16 |
| DOIs | |
| State | Published - Aug 19 2011 |
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ASJC Scopus subject areas
- Organic Chemistry
- Physical and Theoretical Chemistry
- Biochemistry
Cite this
Highly chromic, proton-responsive phenyl pyrimidones. / Dhuguru, Jyothi; Gheewala, Chirag; Kumar, N. S Saleesh; Wilson, James N.
In: Organic Letters, Vol. 13, No. 16, 19.08.2011, p. 4188-4191.Research output: Contribution to journal › Article
}
TY - JOUR
T1 - Highly chromic, proton-responsive phenyl pyrimidones
AU - Dhuguru, Jyothi
AU - Gheewala, Chirag
AU - Kumar, N. S Saleesh
AU - Wilson, James N
PY - 2011/8/19
Y1 - 2011/8/19
N2 - Aryl pyrimidones are pharmacologically relevant compounds whose optical properties have only been partially explored. We report the synthesis and optical characterization of a series of aryl- and diaryl-2(1H)-pyrimidones. The electronic transitions of these chromophores are modulated by the extent of conjugation between the pendant phenyl ring and the pyrimidone core as well as the presence of electron-donating auxochromes. Monoprotonation of the pyrimidone ring results in large hyperchromic and bathochromic shifts as well as switching of fluorescence making these phenyl pyrimidones of interest as sensory materials.
AB - Aryl pyrimidones are pharmacologically relevant compounds whose optical properties have only been partially explored. We report the synthesis and optical characterization of a series of aryl- and diaryl-2(1H)-pyrimidones. The electronic transitions of these chromophores are modulated by the extent of conjugation between the pendant phenyl ring and the pyrimidone core as well as the presence of electron-donating auxochromes. Monoprotonation of the pyrimidone ring results in large hyperchromic and bathochromic shifts as well as switching of fluorescence making these phenyl pyrimidones of interest as sensory materials.
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UR - http://www.scopus.com/inward/citedby.url?scp=80051691876&partnerID=8YFLogxK
U2 - 10.1021/ol2014945
DO - 10.1021/ol2014945
M3 - Article
VL - 13
SP - 4188
EP - 4191
JO - Organic Letters
JF - Organic Letters
SN - 1523-7060
IS - 16
ER -