Muhammad Atta Ur Rehman, Muhammad Adeel, Ume Aiman, Maria Zafar, Khurram Shahzad Munawar, Muhammad Haroon, Rajeh Alotaibi
{"title":"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","authors":"Muhammad Atta Ur Rehman, Muhammad Adeel, Ume Aiman, Maria Zafar, Khurram Shahzad Munawar, Muhammad Haroon, Rajeh Alotaibi","doi":"10.1007/s11224-024-02367-5","DOIUrl":null,"url":null,"abstract":"<p>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 (<b>NTOZ</b>), 2-(4-phenoxyphenyl) oxazole (<b>PPOZ</b>), and 2-(4'-bromo-2,2',6,6'-tetramethyl-[1,1'-biphenyl]-4-yl) oxazole (<b>BMPOZ</b>), for the first time by the palladium-catalyzed Suzuki coupling method. The structures of synthesized products were clarified by employing spectroscopic investigations using <sup>1</sup>H, & <sup>13</sup>C-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 <b>NTOZ</b> compound showed the lowermost band gap (4.764 eV) and uppermost bathochromic shift (307.257 nm) amongst <b>NTOZ</b>, <b>PPOZ</b>, and <b>BMPOZ</b>. Results of global reactivity correspond with FMO outcomes such as <b>NTOZ</b> 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 <b>NTOZ</b>, significant NLO responses such as <i>β</i><sub><i>total</i></sub> = 1.3227 <i>D</i> and <i>β</i><sub><i>total</i></sub> = <i>5.47910</i><sup>–30</sup> <i>esu</i> were investigated, indicating it is an effective NLO material.</p>","PeriodicalId":780,"journal":{"name":"Structural Chemistry","volume":null,"pages":null},"PeriodicalIF":2.1000,"publicationDate":"2024-08-21","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Synthesis of oxazole based chromophores via Pd (0) catalyzed reactions: experimental and computational studies\",\"authors\":\"Muhammad Atta Ur Rehman, Muhammad Adeel, Ume Aiman, Maria Zafar, Khurram Shahzad Munawar, Muhammad Haroon, Rajeh Alotaibi\",\"doi\":\"10.1007/s11224-024-02367-5\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<p>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 (<b>NTOZ</b>), 2-(4-phenoxyphenyl) oxazole (<b>PPOZ</b>), and 2-(4'-bromo-2,2',6,6'-tetramethyl-[1,1'-biphenyl]-4-yl) oxazole (<b>BMPOZ</b>), for the first time by the palladium-catalyzed Suzuki coupling method. The structures of synthesized products were clarified by employing spectroscopic investigations using <sup>1</sup>H, & <sup>13</sup>C-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 <b>NTOZ</b> compound showed the lowermost band gap (4.764 eV) and uppermost bathochromic shift (307.257 nm) amongst <b>NTOZ</b>, <b>PPOZ</b>, and <b>BMPOZ</b>. Results of global reactivity correspond with FMO outcomes such as <b>NTOZ</b> 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 <b>NTOZ</b>, significant NLO responses such as <i>β</i><sub><i>total</i></sub> = 1.3227 <i>D</i> and <i>β</i><sub><i>total</i></sub> = <i>5.47910</i><sup>–30</sup> <i>esu</i> were investigated, indicating it is an effective NLO material.</p>\",\"PeriodicalId\":780,\"journal\":{\"name\":\"Structural Chemistry\",\"volume\":null,\"pages\":null},\"PeriodicalIF\":2.1000,\"publicationDate\":\"2024-08-21\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Structural Chemistry\",\"FirstCategoryId\":\"92\",\"ListUrlMain\":\"https://doi.org/10.1007/s11224-024-02367-5\",\"RegionNum\":4,\"RegionCategory\":\"化学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"Q3\",\"JCRName\":\"CHEMISTRY, MULTIDISCIPLINARY\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Structural Chemistry","FirstCategoryId":"92","ListUrlMain":"https://doi.org/10.1007/s11224-024-02367-5","RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q3","JCRName":"CHEMISTRY, MULTIDISCIPLINARY","Score":null,"Total":0}
Synthesis of oxazole based chromophores via Pd (0) catalyzed reactions: experimental and computational studies
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 = 5.47910–30esu were investigated, indicating it is an effective NLO material.
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.