Pyrimidine-Core Extended π-Systems: General Synthesis and Interesting Fluorescent Properties
Publication type: Journal Article
Publication date: 2004-11-06
scimago Q1
wos Q1
SJR: 5.554
CiteScore: 22.5
Impact factor: 15.6
ISSN: 00027863, 15205126
PubMed ID:
15563163
General Chemistry
Catalysis
Biochemistry
Colloid and Surface Chemistry
Abstract
We have developed a simple but powerful synthetic strategy that permits the assembly of π-systems onto a pyrimidine core in a programmable and diversity-oriented format. The nucleophilic addition of ArLi to 2-methylthiopyrimidine, followed by 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) oxidation, resulted in the production of 4-aryl-2-methylthiopyrimidines. The iterative reaction sequence then gave 4,6-diaryl-2-methylthiopyrimidines. The resulting adduct was further allowed to react with ArMgBr under the catalytic influence of NiCl2(dppe) to afford 2,4,6-triarylpyrimidines. By following this synthetic scheme, interesting pyrimidine-core π-systems were rapidly constructed in a programmable fashion. The successful discovery of a number of interesting fluorescent materials and properties (e.g., solvatofluorochromism) speaks well for the potential of our platform strategy in the development of functional organic materials.
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Itami K., Yamazaki D., Yoshida J. Pyrimidine-Core Extended π-Systems: General Synthesis and Interesting Fluorescent Properties // Journal of the American Chemical Society. 2004. Vol. 126. No. 47. pp. 15396-15397.
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Itami K., Yamazaki D., Yoshida J. Pyrimidine-Core Extended π-Systems: General Synthesis and Interesting Fluorescent Properties // Journal of the American Chemical Society. 2004. Vol. 126. No. 47. pp. 15396-15397.
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TY - JOUR
DO - 10.1021/ja044923w
UR - https://doi.org/10.1021/ja044923w
TI - Pyrimidine-Core Extended π-Systems: General Synthesis and Interesting Fluorescent Properties
T2 - Journal of the American Chemical Society
AU - Itami, Kenichiro
AU - Yamazaki, Daisuke
AU - Yoshida, J.
PY - 2004
DA - 2004/11/06
PB - American Chemical Society (ACS)
SP - 15396-15397
IS - 47
VL - 126
PMID - 15563163
SN - 0002-7863
SN - 1520-5126
ER -
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BibTex (up to 50 authors)
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@article{2004_Itami,
author = {Kenichiro Itami and Daisuke Yamazaki and J. Yoshida},
title = {Pyrimidine-Core Extended π-Systems: General Synthesis and Interesting Fluorescent Properties},
journal = {Journal of the American Chemical Society},
year = {2004},
volume = {126},
publisher = {American Chemical Society (ACS)},
month = {nov},
url = {https://doi.org/10.1021/ja044923w},
number = {47},
pages = {15396--15397},
doi = {10.1021/ja044923w}
}
Cite this
MLA
Copy
Itami, Kenichiro, et al. “Pyrimidine-Core Extended π-Systems: General Synthesis and Interesting Fluorescent Properties.” Journal of the American Chemical Society, vol. 126, no. 47, Nov. 2004, pp. 15396-15397. https://doi.org/10.1021/ja044923w.