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<p>Advanced organic NLO materials are increasingly important for modern telecommunication, primarily due to their short optical response time compared to inorganic alternatives. Here, we synthesize ethyl 2-((4-bromobenzyl)oxy)benzoate/4-bromobenzyl 1-naphthoate by reacting ethyl 2-hydroxybenzoate/Naphthoic acid and 4-bromobenzyl bromide with commercially available bases K<sub>2</sub>CO<sub>3</sub>/Na<sub>2</sub>CO<sub>3</sub> in dry acetone/DMF. Afterward, we subsequently synthesized a series of ethyl 2-([1,1’-biphenyl]-4-ylmethoxy)benzoates (7a-7c) and [1,1’-biphenyl]-4-ylmethyl 1-naphthoates (10a-10&#xa0;h) through palladium (0) catalyzed Suzuki coupling between ethyl 2-((4-bromobenzyl)oxy)benzoate/4-bromobenzyl 1-naphthoates with a number of heteroaryl and substituted arylated boronic acids. Characteristics features related to structure of synthesized molecules (7a-7c, 10a-10&#xa0;h) were confirmed by DFT calculations, geometrical optimization, and thermodynamic parameters such as NLO optical behavior, FMO, MESP maps, and reactivity descriptors from PBE0 D3BJ/def2-TZVP/SMD1,4-dioxane. Calculations of energy gaps of HOMO, LUMO orbitals, and hyperpolarizabilities were used to analyze the stability of molecules and the behavior of NLOs. Based on the computed data, compound 10&#xa0;g exhibits the highest hyperpolarizability value (<i>β</i> = 3294.12 a. u.) and the smallest HOMO–LUMO energy gap (4.13&#xa0;eV), indicating both strong nonlinear optical (NLO) activity. In contrast, compound 7c shows the largest energy gap (5.23&#xa0;eV) and the lowest hyperpolarizability (<i>β</i> = 714.59 a. u.), reflecting weaker NLO response.</p>

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Palladium catalyzed facile synthesis of ethyl 2-([1,1’-biphenyl]-4-ylmethoxy)benzoates and [1,1’-biphenyl]-4-ylmethyl 1-naphthoates: spectroscopic, thermodynamic, and NLO properties

  • 期刊论文

  • 发表日期：

    2026年4月21日

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  • Sidra Raza,
  • Adeel Mubarik,
  • Nasir Rasool,
  • Almeera Zia,
  • Matloob Ahmad,
  • Maria Sohail,
  • Aqsa Kanwal,
  • Muhammad Fakhar U. Zaman,
  • Muhammad Imran

摘要

Advanced organic NLO materials are increasingly important for modern telecommunication, primarily due to their short optical response time compared to inorganic alternatives. Here, we synthesize ethyl 2-((4-bromobenzyl)oxy)benzoate/4-bromobenzyl 1-naphthoate by reacting ethyl 2-hydroxybenzoate/Naphthoic acid and 4-bromobenzyl bromide with commercially available bases K2CO3/Na2CO3 in dry acetone/DMF. Afterward, we subsequently synthesized a series of ethyl 2-([1,1’-biphenyl]-4-ylmethoxy)benzoates (7a-7c) and [1,1’-biphenyl]-4-ylmethyl 1-naphthoates (10a-10 h) through palladium (0) catalyzed Suzuki coupling between ethyl 2-((4-bromobenzyl)oxy)benzoate/4-bromobenzyl 1-naphthoates with a number of heteroaryl and substituted arylated boronic acids. Characteristics features related to structure of synthesized molecules (7a-7c, 10a-10 h) were confirmed by DFT calculations, geometrical optimization, and thermodynamic parameters such as NLO optical behavior, FMO, MESP maps, and reactivity descriptors from PBE0 D3BJ/def2-TZVP/SMD1,4-dioxane. Calculations of energy gaps of HOMO, LUMO orbitals, and hyperpolarizabilities were used to analyze the stability of molecules and the behavior of NLOs. Based on the computed data, compound 10 g exhibits the highest hyperpolarizability value (β = 3294.12 a. u.) and the smallest HOMO–LUMO energy gap (4.13 eV), indicating both strong nonlinear optical (NLO) activity. In contrast, compound 7c shows the largest energy gap (5.23 eV) and the lowest hyperpolarizability (β = 714.59 a. u.), reflecting weaker NLO response.