Synthesis of oxazole based chromophores via Pd (0) catalyzed reactions: experimental and computational studies

IF 2.1 4区 化学 Q3 CHEMISTRY, MULTIDISCIPLINARY
Muhammad Atta Ur Rehman, Muhammad Adeel, Ume Aiman, Maria Zafar, Khurram Shahzad Munawar, Muhammad Haroon, Rajeh Alotaibi
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Abstract

Derivatives of aryl and hetero-aryl substituted oxazoles have several uses in agrochemicals, pharmaceuticals, and nonlinear optics (NLO). This study reports the synthesis and non-linear optical response (NLO) of three new compounds, viz., 2-(naphthalen-2-yl) oxazole (NTOZ), 2-(4-phenoxyphenyl) oxazole (PPOZ), and 2-(4'-bromo-2,2',6,6'-tetramethyl-[1,1'-biphenyl]-4-yl) oxazole (BMPOZ), for the first time by the palladium-catalyzed Suzuki coupling method. The structures of synthesized products were clarified by employing spectroscopic investigations using 1H, & 13C-NMR, FT-IR, and UV-visible. The DFT studies were conducted at the M06/6-31G (d,p) functional to visualize NLO properties. Various analyses, including frontier molecular orbitals (FMOs), natural bond orbitals (NBOs), transition density matrix (TDM), and density of state (DOS), were conducted to learn more about the NLO response of the aforesaid compounds. The results indicated that the NTOZ compound showed the lowermost band gap (4.764 eV) and uppermost bathochromic shift (307.257 nm) amongst NTOZ, PPOZ, and BMPOZ. Results of global reactivity correspond with FMO outcomes such as NTOZ with a lower band gap, which displayed lower hardness (2.382 eV) and higher softness (0.2099 eV) data. Owing to the unique properties of NTOZ, significant NLO responses such as βtotal = 1.3227 D and βtotal = 5.47910–30 esu were investigated, indicating it is an effective NLO material.

Abstract Image

通过 Pd (0) 催化反应合成基于噁唑的发色团:实验和计算研究
芳基和杂芳基取代的噁唑衍生物在农用化学品、制药和非线性光学(NLO)方面有多种用途。本研究报告了三种新化合物的合成和非线性光学响应(NLO),即2-(naphthalen-2-yl) oxazole (NTOZ)、2-(4-phenoxyphenyl) oxazole (PPOZ) 和 2-(4'-bromo-2,2',6,6'-tetramethyl-[1,1'-biphenyl]-4-yl) oxazole (BMPOZ)。通过使用 1H、& 13C-NMR、傅立叶变换红外光谱和紫外可见光谱进行光谱研究,澄清了合成产物的结构。在 M06/6-31G (d,p) 函数下进行了 DFT 研究,以观察 NLO 特性。为了进一步了解上述化合物的 NLO 响应,还进行了各种分析,包括前沿分子轨道 (FMO)、天然键轨道 (NBO)、过渡密度矩阵 (TDM) 和状态密度 (DOS)。结果表明,在 NTOZ、PPOZ 和 BMPOZ 化合物中,NTOZ 化合物的带隙(4.764 eV)最小,浴色偏移(307.257 nm)最大。全局反应性的结果与 FMO 的结果一致,如 NTOZ 具有较低的带隙,显示出较低的硬度(2.382 eV)和较高的软度(0.2099 eV)数据。由于 NTOZ 的独特性质,研究人员研究了显著的 NLO 反应,如 βtotal = 1.3227 D 和 βtotal = 5.47910-30 esu,这表明它是一种有效的 NLO 材料。
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来源期刊
Structural Chemistry
Structural Chemistry 化学-化学综合
CiteScore
3.80
自引率
11.80%
发文量
227
审稿时长
3.7 months
期刊介绍: Structural Chemistry is an international forum for the publication of peer-reviewed original research papers that cover the condensed and gaseous states of matter and involve numerous techniques for the determination of structure and energetics, their results, and the conclusions derived from these studies. The journal overcomes the unnatural separation in the current literature among the areas of structure determination, energetics, and applications, as well as builds a bridge to other chemical disciplines. Ist comprehensive coverage encompasses broad discussion of results, observation of relationships among various properties, and the description and application of structure and energy information in all domains of chemistry. We welcome the broadest range of accounts of research in structural chemistry involving the discussion of methodologies and structures,experimental, theoretical, and computational, and their combinations. We encourage discussions of structural information collected for their chemicaland biological significance.
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