1,1-Difluoro-1,3,5,2-triazaborinines containing benzo-fused imidazo-, oxazolo-, and thiazolo-pyrimido as a new luminescent framework

IF 4.1 3区工程技术 Q2 CHEMISTRY, APPLIED

Dyes and Pigments Pub Date : 2024-09-05 DOI:10.1016/j.dyepig.2024.112435

Ricardo R.C. Cassol , Fábio M. Luz , Érica T.O. Machado , Victor S. Pereira , Clarissa P. Frizzo , Marcos A.P. Martins , Nilo Zanatta , Victor M. Deflon , Rafaela C. Cunha , Bernardo A. Iglesias , Helio G. Bonacorso

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引用次数: 0

Abstract

In this paper, we present for the first time an efficient method for synthesizing three novel tetra–coordinated BF₂ complexes, specifically 6,6-difluoro-2,4-dimethyl-6H-5λ⁴,6λ⁴-benzo [4,5]imidazo(oxazolo/thiazolo)[3,2-c]pyrimido [2,1-f][1,3,5,2]triazaborinines (4a–c). These compounds were synthesized via the reaction of selected N-(4,6-dimethylpyrimidin-2-yl)-benzo[d]imidazo(oxazolo/thiazolo)-2-amines (3a–c) with BF₃·OEt₂, employing Et₃N as a base. Optimized yields ranging from 64 to 69 % were achieved when the reactions were conducted in anhydrous CHCl₃ at room temperature for 24 h. The structural elucidation of BF₂ complexes 4a-c was performed through multinuclear NMR, FTIR, SC-XRD, and HRMS techniques. These compounds demonstrated thermal stability up to 150 °C as evidenced by thermogravimetric analysis. The spectroscopic properties (in both solution and solid states) and the electrochemical properties of the synthesized derivatives were thoroughly investigated using UV–Vis spectroscopy, steady-state, time-resolved fluorescence emission, TD-DFT calculations, and redox potential measurements. The results of this study highlighted a dependence of the compounds’ properties on the heteroatom (NH, O, or S) present within the heterocyclic skeleton.

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1,1-Difluoro-1,3,5,2-triazaborinines containing benzo-fused imidazo-, oxazolo, and thiazolo-pyrimido as a new luminescent framework含有苯并融合咪唑、恶唑和噻唑嘧啶作为新的发光框架

在本文中，我们首次提出了合成三种新型四配位 BF2 复合物的有效方法，特别是 6,6-二氟-2,4-二甲基-6H-5λ4,6λ4-苯并 [4,5]咪唑(恶唑/噻唑)[3,2-c]嘧啶并 [2,1-f][1,3,5,2]triazaborinines (4a-c)。这些化合物是以 Et3N 为碱，通过选定的 N-(4,6-二甲基嘧啶-2-基)-苯并[d]咪唑(恶唑/噻唑)-2-胺 (3a-c) 与 BF3-OEt2 反应合成的。通过多核 NMR、FTIR、SC-XRD 和 HRMS 技术阐明了 BF2 复合物 4a-c 的结构。热重分析表明，这些化合物具有高达 150 °C 的热稳定性。利用紫外可见光谱、稳态、时间分辨荧光发射、TD-DFT 计算和氧化还原电位测量，对合成衍生物的光谱特性（溶液和固体状态）和电化学特性进行了深入研究。研究结果表明，化合物的性质取决于杂环骨架中存在的杂原子（NH、O 或 S）。

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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.