Photofunctional fulvene ligand, boron complex and application
A technology of optical functions and complexes, which is applied in the direction of preparation of organic compounds, condensation preparation of carbonyl compounds, compounds containing elements of group 3/13 of the periodic table, etc., can solve the problem of fewer boron complexes and achieve high electron mobility , high application prospects, and good stimulus responsiveness
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Embodiment 1
[0078] ((5Z)-3-tert-butyl-5-(hydroxy(naphthalene-2-yl)methylene)cyclopent-1,3-dienyl)(naphthalene-3-yl)methanone (YCX-1 )Synthesis.
[0079] The synthetic route is:
[0080]
[0081] Under nitrogen protection, 6,6-dimethylfulvene (3.025 g, 28.5 mmol) was mixed with 20 mL of anhydrous ether, and 22 mL of methyllithium was added to the mixture, stirred for 45 min, and the solution turned white. 2-Naphthoyl chloride (3.6g, 19.0mmol) was added dropwise into the mixed solution, the solution changed color, stirred overnight, filtered with suction, washed with petroleum ether, acidified with hydrochloric acid, stirred for 12h, filtered with suction to obtain a crude product. The residue was purified by column chromatography using dichloromethane as eluent to give the product as a yellow solid (2.725 g, 67.3%).
[0082] Synthesis of a boron complex (B-YCX-1) based on the YCX-1 ligand.
[0083] The synthetic route is as follows:
[0084]
[0085] Under nitrogen protection, ad...
Embodiment 2
[0088] ((5Z)-3-tert-butyl-5-(hydroxy(2-methoxynaphthalene-6-yl)methylene)cyclopent-1,3-dienyl)(2-methoxynaphthalene- Synthesis of 6-yl)methanone (YCX-2).
[0089] The synthetic route is as follows:
[0090]
[0091]Under nitrogen protection, 6,6-dimethylfulvene (3.025 g, 28.5 mmol) was mixed with 20 mL of anhydrous ether, and 22 mL of methyllithium was added to the mixture, stirred for 45 min, and the solution turned white. Add 6-methoxy-2-naphthoyl chloride (4.19g, 19.0mmol) dropwise into the mixed solution, the solution changes color, stir overnight, filter with suction, wash with petroleum ether, acidify with hydrochloric acid, stir for 12h, and filter with suction to obtain crude product. The residue was purified by column chromatography using dichloromethane as eluent to give the product as a yellow solid (0.86 g, 38.9%).
[0092] Synthesis of a boron complex (B-YCX-2) based on the YCX-2 ligand.
[0093] The synthetic route is as follows:
[0094]
[0095] Unde...
Embodiment 3
[0098] ((5Z)-3-tert-butyl-5-(hydroxy(4-methoxyphenyl)methylene)cyclopent-1,3-dienyl)(4-methoxyphenyl)methanone (FUXI-OCH 3 )Synthesis.
[0099] The synthetic route is as follows:
[0100]
[0101] Under the protection of nitrogen, 6,6-dimethylfulvene (0.302g, 2.85mmol) was mixed with 20mL of anhydrous ether, and 22mL of methyllithium was added to the mixture, stirred for 45min, and the solution turned white. P-methoxybenzoyl chloride (0.324g, 1.9mmol) was added dropwise into the mixed solution, the solution changed color, stirred overnight, filtered with suction, washed with petroleum ether, acidified with hydrochloric acid, stirred for 12h, filtered with suction to obtain a crude product. The residue was purified by column chromatography using dichloromethane as eluent to give the product as a yellow solid (0.197 g, 53%).
[0102] Based on FUXI-OCH 3 Ligand boron complexes (FUXI-OCH 3 - Synthesis of B).
[0103] The synthetic route is as follows:
[0104]
[0105...
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