Lewis acid-catalyzed chemo- and stereoselective addition of pyrroles to skipped diynones: en route to novel pyrrole-based ketocyanine dyes and alkyne-tethered enones

IF 4.1 3区工程技术 Q2 CHEMISTRY, APPLIED Dyes and Pigments Pub Date : 2024-06-18 DOI:10.1016/j.dyepig.2024.112293

Marina Yu. Dvorko, Igor’ A. Ushakov, Dmitrii A. Shabalin

引用次数: 0

Abstract

The first chemo- and stereoselective syntheses of hitherto unknown pyrrole-based β,β′-disubstituted ketocyanine dyes and alkyne-tethered enones through Lewis acid-catalyzed addition of pyrroles to skipped diynones (penta-1,4-diyn-3-ones) are described. The protocols feature a good substrate tolerance, mild reaction conditions, and high yields of target products. A wide synthetic utility of synthesized alkyne-tethered enones as novel building blocks is demonstrated by the synthesis of diverse pyrrole-containing compounds. The UV–vis absorption properties for selected representatives of novel adducts are studied to preliminary access their potential as photoinitiators/sensitizers in visible light induced polymerization.

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路易斯酸催化的吡咯与跳过的二炔酮的化学和立体选择性加成：通向新型吡咯基酮腈染料和炔拴烯酮的途径

通过路易斯酸催化吡咯与跳过的二炔酮（penta-1,4-diyn-3-ones）的加成，首次化学和立体选择性合成了迄今未知的基于吡咯的β,β′-二取代酮氰染料和炔烃系烯酮。这些方案具有良好的底物耐受性、温和的反应条件和高产率的目标产物。通过合成多种含吡咯的化合物，证明了合成的炔拴烯酮作为新型构筑基块具有广泛的合成用途。研究了选定的新型加合物代表的紫外-可见吸收特性，以初步了解它们在可见光诱导聚合中作为光引发剂/敏化剂的潜力。

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来源期刊

Dyes and Pigments 工程技术-材料科学：纺织

CiteScore

8.20

自引率

13.30%

发文量

933

审稿时长

33 days

期刊介绍： Dyes and Pigments covers the scientific and technical aspects of the chemistry and physics of dyes, pigments and their intermediates. Emphasis is placed on the properties of the colouring matters themselves rather than on their applications or the system in which they may be applied. Thus the journal accepts research and review papers on the synthesis of dyes, pigments and intermediates, their physical or chemical properties, e.g. spectroscopic, surface, solution or solid state characteristics, the physical aspects of their preparation, e.g. precipitation, nucleation and growth, crystal formation, liquid crystalline characteristics, their photochemical, ecological or biological properties and the relationship between colour and chemical constitution. However, papers are considered which deal with the more fundamental aspects of colourant application and of the interactions of colourants with substrates or media. The journal will interest a wide variety of workers in a range of disciplines whose work involves dyes, pigments and their intermediates, and provides a platform for investigators with common interests but diverse fields of activity such as cosmetics, reprographics, dye and pigment synthesis, medical research, polymers, etc.