Photochemistry of a 9-Dithianyl-Pyronin Derivative: A Cornucopia of Reaction Intermediates Lead to Common Photoproducts.,ChemPlusChem

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Photochemistry of a 9-Dithianyl-Pyronin Derivative: A Cornucopia of Reaction Intermediates Lead to Common Photoproducts.
ChemPlusChem ( IF 3.0 ) Pub Date : 2020-07-30 , DOI: 10.1002/cplu.202000370
Marek Martínek _{1,

2} , Jiří Váňa ₃ , Peter Šebej ₂ , Rafael Navrátil ₄ , Tomáš Slanina _{1,

2} , Lucie Ludvíková _{1,

2} , Jana Roithová ₅ , Petr Klán _{1,

2}

Affiliation

Leaving groups attached to the meso‐methyl position of many common dyes, such as xanthene, BODIPY, or pyronin derivatives, can be liberated upon irradiation with visible light. However, the course of phototransformations of such photoactivatable systems can be quite complex and the identification of reaction intermediates or even products is often neglected. This paper exemplifies the photochemistry of a 9‐dithianyl‐pyronin derivative, which undergoes an oxidative transformation at the meso‐position to give a 3,6‐diamino‐9H‐xanthen‐9‐one derivative, formic acid, and carbon monoxide as the main photoproducts. The course of this multi‐photon multi‐step reaction was studied under various conditions by steady‐state and time‐resolved optical spectroscopy, mass spectrometry and NMR spectroscopy to understand the effects of solvents and molecular oxygen on individual steps. Our analyses have revealed the existence of many intermediates and their interrelationships to provide a complete picture of the transformation, which can bring new inputs to a rational design of new photoactivatable pyronin or xanthene derivatives.

中文翻译：

9-Dithianyl-Pyronin衍生物的光化学：反应中间体的聚宝盆导致常见的光产物。

留下附着于基团的内消旋许多常见染料，例如呫吨-甲基位置，BODIPY，或焦宁衍生物，可在用可见光照射解放。但是，这种可光活化系统的光转化过程可能非常复杂，并且常常忽略了对反应中间体甚至产物的鉴定。本文举例说明了9-噻烷基-焦宁衍生物的光化学，其经历在氧化转化的内消旋-位，得到3,6-二氨基-9- ħ黄嘌呤9一衍生物，甲酸和一氧化碳为主要光产物。通过稳态和时间分辨光谱，质谱和NMR光谱在各种条件下研究了这种多光子多步反应的过程，以了解溶剂和分子氧在各个步骤中的作用。我们的分析揭示了许多中间体的存在以及它们之间的相互关系，以提供对转化的完整描述，这可以为合理设计新的光活化性吡喃酮或or吨衍生物带来新的投入。

更新日期：2020-10-02

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