2,5-Di(het)arylpyridines: synthesis by ‘‘1,2,4-triazine’’ methodology and photophysical properties

IF 1.4 4区 化学 Q3 CHEMISTRY, ORGANIC
Alexei P. Krinochkin, Albert F. Khasanov, Maria I. Valieva, Ekaterina A. Kudryashova, Mallikarjuna R. Guda, Dmitry S. Kopchuk, Olga V. Shabunina, Nataliya N. Mochulskaya, Pavel A. Slepukhin, Grigory V. Zyryanov, Oleg N. Chupakhin
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引用次数: 0

Abstract

The method for the preparation of 3,6-disubstituted 1,2,4-triazines based on condensation reaction between easily available α-imino esters and isonitrosoacetophenone hydrazones was reported. The significant differences in reaction conditions, ratio of products, and yields between the developed method and the earlier reported approach were demonstrated. The corresponding 2,5-disubstituted pyridines were synthesized from the prepared 1,2,4-triazines, and their photophysical properties were studied. Studies of the photo-physical properties revealed low and moderate luminescence quantum yields, and negligible solvatochromic behavior in case of 4-methoxyphenylpyridine derivative due to the role of donating methoxy group, however, with a low linearity of a Lippert–Mataga plot. Nevertheless, 2,5-disubstituted pyridines are of interest due to simple protocols of synthesis, moderate photophysical properties, and potential applicability in different scientific and industrial areas.

Abstract Image

2,5-二(噻)芳基吡啶:用 "1,2,4-三嗪 "方法合成和光物理特性
报告了基于易得的 α-亚氨基酯和异亚硝基苯乙酮肼之间的缩合反应制备 3,6-二取代的 1,2,4-三嗪的方法。结果表明,所开发的方法与早先报道的方法在反应条件、产物比例和收率方面存在明显差异。利用制备的 1,2,4-三嗪合成了相应的 2,5-二取代吡啶,并对其光物理性质进行了研究。对光物理性质的研究表明,4-甲氧基苯基吡啶衍生物的发光量子产率较低且适中,由于甲氧基的供体作用,其溶解变色行为可忽略不计,但其 Lippert-Mataga 图的线性度较低。尽管如此,2,5-二取代吡啶因其简单的合成方法、适中的光物理性质以及在不同科学和工业领域的潜在应用而备受关注。
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来源期刊
CiteScore
2.90
自引率
13.30%
发文量
98
审稿时长
1 months
期刊介绍: The international journal Chemistry of Heterocyclic Compounds publishes original papers, short communications, reviews, and mini-reviews dealing with problems in the field of heterocyclic chemistry in Russian and English. The Journal also publishes reviews and annotations on new books and brief reports on conferences in the field of heterocyclic chemistry, as well as commemo­ra­tives dedicated to prominent heterocyclic chemists.
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