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<p>A new series of push-pull chromophores (<b>1</b>–<b>6</b>) with ferrocene and methoxyphenyl donors and π-acceptor groups were synthesized and characterized. The chromophores (<b>1</b>–<b>3</b>) [Fc-C = C(CN)-(C<sub>6</sub>H<sub>4</sub>)-(C<sub>6</sub>H<sub>3</sub>)-R {R = H (<b>1</b>), OCH<sub>3</sub> (<b>2</b>), CF<sub>3</sub> (<b>3</b>)}] and D-D’-π-A (<b>4</b>–<b>6</b>), [Fc-(OCH<sub>3</sub>-C<sub>6</sub>H<sub>4</sub>)-C = CH=CN-(C<sub>6</sub>H<sub>4</sub>)-(C<sub>6</sub>H<sub>3</sub>)-R {R = H (<b>4</b>), OCH<sub>3</sub> (<b>5</b>), CF<sub>3</sub> (<b>6</b>)}] were studied for their photophysical and nonlinear optical (NLO) properties. Single-crystal X-ray diffraction studies confirmed the crystal structures of selected chromophores <b>1</b>, <b>3</b>, <b>4</b>, and <b>6</b>, showing various non-covalent interactions such as H-bonding and C-H⋅⋅⋅⋅⋅π interactions. The second-order nonlinear optical (NLO) response of chromophore <b>6</b> shows significantly enhanced second-harmonic generation (SHG) efficiency, approximately 2.9 times higher than that of standard potassium dihydrogen phosphate (KDP), due to the extended π-conjugation results in deviation of chromophores from planarity, which prevents antiparallel alignment in the bulk. To gain deeper insight into structure-property relationships, bond length alternation (BLA) values were evaluated based on BLA, correlating with NLO performance. Furthermore, density functional theory (DFT) calculations at the B3LYP/6–31 + G** level included both static and dynamic energy-dependent hyperpolarizabilities, showing good agreement with experimental optical and NLO results.</p>

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Exploring the impact of substituents and π-conjugation on structural, optical and nonlinear optical studies in ferrocene-appended D-π-A and D-D’-π-A chromophores

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  • 发表日期：

    2026年2月18日

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  • Vadakkalur Sampath Chithra,
  • Selvam Prabu,
  • P. P. Sanak Archana,
  • Nallasamy Palanisami

摘要

A new series of push-pull chromophores (1–6) with ferrocene and methoxyphenyl donors and π-acceptor groups were synthesized and characterized. The chromophores (1–3) [Fc-C = C(CN)-(C6H4)-(C6H3)-R {R = H (1), OCH3 (2), CF3 (3)}] and D-D’-π-A (4–6), [Fc-(OCH3-C6H4)-C = CH=CN-(C6H4)-(C6H3)-R {R = H (4), OCH3 (5), CF3 (6)}] were studied for their photophysical and nonlinear optical (NLO) properties. Single-crystal X-ray diffraction studies confirmed the crystal structures of selected chromophores 1, 3, 4, and 6, showing various non-covalent interactions such as H-bonding and C-H⋅⋅⋅⋅⋅π interactions. The second-order nonlinear optical (NLO) response of chromophore 6 shows significantly enhanced second-harmonic generation (SHG) efficiency, approximately 2.9 times higher than that of standard potassium dihydrogen phosphate (KDP), due to the extended π-conjugation results in deviation of chromophores from planarity, which prevents antiparallel alignment in the bulk. To gain deeper insight into structure-property relationships, bond length alternation (BLA) values were evaluated based on BLA, correlating with NLO performance. Furthermore, density functional theory (DFT) calculations at the B3LYP/6–31 + G** level included both static and dynamic energy-dependent hyperpolarizabilities, showing good agreement with experimental optical and NLO results.