Synthesis of BODIPY-pyrrolo[3,4-b]pyridin-5-ones via Ugi-Zhu/cascade reactions and studies of fluorescence response toward viscosity.

IF 3.8 3区化学 Q2 CHEMISTRY, MULTIDISCIPLINARY

Frontiers in Chemistry Pub Date : 2024-10-18 eCollection Date: 2024-01-01 DOI:10.3389/fchem.2024.1488933

Julio C Flores-Reyes, Annia Galano, Sandra M Rojas-Montoya, Luis Blancarte-Carrazco, Elba Xochitiotzi-Flores, Héctor García-Ortega, Norberto Farfán, Alejandro Islas-Jácome, Eduardo González-Zamora

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Abstract

A series of seven new meso-phenyl BODIPY-pyrrolo[3,4-b]pyridin-5-one conjugates were synthesized in one experimental step by using a Sc(III)-catalyzed Ugi-Zhu three-component reaction coupled to a cascade sequence (aza Diels-Alder/N-acylation/aromatization) as post-MCR functionalization process. Further experimental studies were performed behind understanding the fluorescence response toward viscosity. All compounds exhibited a linear response between increasing viscosity (DMSO and glycerol mixtures) and fluorescence intensity. The different substituents also influenced the photophysical properties. Furthermore, in DMSO all compounds exhibited dual emission. Each band is attributed to the pyrrolo[3,4-b]pyridin-5-one and BODIPY moieties, respectively. The electronic structure of all compounds was computed by DFT and TD-DFT calculations, allowing to determine the molecular orbitals involved in the electronic transitions.

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通过乌基-朱/级联反应合成 BODIPY-吡咯并[3,4-b]吡啶-5-酮并研究荧光对粘度的响应。

通过使用 Sc(III)-catalyzed Ugi-Zhu 三组分反应与级联序列（氮杂 Diels-Alder/N-酰化/芳香化）作为后 MCR 功能化过程，在一个实验步骤中合成了一系列七种新的介苯基 BODIPY-吡咯并[3,4-b]吡啶-5-酮共轭物。为了了解荧光对粘度的响应，我们进行了进一步的实验研究。所有化合物都表现出粘度（二甲基亚砜和甘油混合物）增加与荧光强度之间的线性响应。不同的取代基也会影响光物理特性。此外，在二甲基亚砜中，所有化合物都表现出双重发射。每个条带分别归因于吡咯并[3,4-b]吡啶-5-酮和 BODIPY 分子。所有化合物的电子结构都是通过 DFT 和 TD-DFT 计算得出的，从而确定了电子跃迁所涉及的分子轨道。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

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来源期刊

Frontiers in Chemistry Chemistry-General Chemistry

CiteScore

8.50

自引率

3.60%

发文量

1540

审稿时长

12 weeks

期刊介绍： Frontiers in Chemistry is a high visiblity and quality journal, publishing rigorously peer-reviewed research across the chemical sciences. Field Chief Editor Steve Suib at the University of Connecticut is supported by an outstanding Editorial Board of international researchers. This multidisciplinary open-access journal is at the forefront of disseminating and communicating scientific knowledge and impactful discoveries to academics, industry leaders and the public worldwide. Chemistry is a branch of science that is linked to all other main fields of research. The omnipresence of Chemistry is apparent in our everyday lives from the electronic devices that we all use to communicate, to foods we eat, to our health and well-being, to the different forms of energy that we use. While there are many subtopics and specialties of Chemistry, the fundamental link in all these areas is how atoms, ions, and molecules come together and come apart in what some have come to call the “dance of life”. All specialty sections of Frontiers in Chemistry are open-access with the goal of publishing outstanding research publications, review articles, commentaries, and ideas about various aspects of Chemistry. The past forms of publication often have specific subdisciplines, most commonly of analytical, inorganic, organic and physical chemistries, but these days those lines and boxes are quite blurry and the silos of those disciplines appear to be eroding. Chemistry is important to both fundamental and applied areas of research and manufacturing, and indeed the outlines of academic versus industrial research are also often artificial. Collaborative research across all specialty areas of Chemistry is highly encouraged and supported as we move forward. These are exciting times and the field of Chemistry is an important and significant contributor to our collective knowledge.