Synthetic and Computational Study of Four-Coordinate B,B-Diaryl 8-Aminoquinolate Complexes

doi:10.6023/cjoc202108040

Chinese Journal of Organic Chemistry ›› 2022, Vol. 42 ›› Issue (3): 812-818.DOI: 10.6023/cjoc202108040 Previous Articles Next Articles

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8-氨基喹啉骨架螯合的四配位B,B-二芳基络合物的合成与计算研究

丁思懿^a, 祖维赛^b, 苗宗成^a^,^*(), 徐亮^b^,^*()

a 西京学院理学院西安市先进光电子材料与能源转换器件重点实验室西安 710123
b 石河子大学化学化工学院新疆兵团化工绿色过程重点实验室新疆石河子 832003

收稿日期:2021-08-20 修回日期:2021-10-27 发布日期:2021-11-25
通讯作者: 苗宗成, 徐亮
基金资助:
国家自然科学基金(21901214); 国家自然科学基金(21963010); 陕西省自然科学基金(2020JQ-918)

Synthetic and Computational Study of Four-Coordinate B,B-Diaryl 8-Aminoquinolate Complexes

Siyi Ding^a, Weisai Zu^b, Zongcheng Miao^a(), Liang Xu^b()

a Xi'an Key Laboratory of Advanced Photo-electronics Materials and Energy Conversion Device, School of Science, Xijing University, Xi'an 710123
b Key Laboratory for Green Processing of Chemical Engineering of Xinjiang Bingtuan, School of Chemistry and Chemical Engineering, Shihezi University, Shihezi, Xinjiang 832003

Received:2021-08-20 Revised:2021-10-27 Published:2021-11-25
Contact: Zongcheng Miao, Liang Xu
Supported by:
National Natural Science Foundation of China(21901214); National Natural Science Foundation of China(21963010); Natural Science Foundation of Shaanxi Province(2020JQ-918)

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Abstract

Despite the wide application of four-coordinate organoboron compounds as fluorescent materials, the synthesis of such complexes, which contain two aryl groups on the boron centers, is relatively limited by the need for sensitive organometallic reagents. Herein, using stable and commercially available aryl trifluoroborate potassium salts as complexation reagents, a series of aminoquinolate-framed diarylboron complexes, which were difficult to access previously, have been obtained in moderate to excellent yields. Furthermore, density functional theory (DFT) study of the obtained complex shows its molecular orbital distribution.

Key words: photocatalyst, trifluoroborate potassium, four-coordinate organoboron, theoretical calculation

Cite this article

Siyi Ding, Weisai Zu, Zongcheng Miao, Liang Xu. Synthetic and Computational Study of Four-Coordinate B,B-Diaryl 8-Aminoquinolate Complexes[J]. Chinese Journal of Organic Chemistry, 2022, 42(3): 812-818.

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Fig. & Tab. 5

References 18

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Entry	Variations from the ‘standard’ conditions	Yield^b/%
	No 4-toluenesulfonyl chloride	5
	No Mn	25
	No Na₂CO₃	84
	K₂CO₃ instead of Na₂CO₃	80
	NaHCO₃ instead of Na₂CO₃	91
	NaOMe instead of Na₂CO₃	N.D.
	DMSO instead of CH₃CN	N.D.
	DMF instead of CH₃CN	53
	Toluene instead of CH₃CN	Trace
	1,4-Dioxane instead of CH₃CN	24
	Fe instead of Mn	32
	MnCl₂ instead of Mn	N.D.
	80 ℃ instead of 130 ℃	Trace

Entry	Variations from the ‘standard’ conditions	Yield^b/%
	No 4-toluenesulfonyl chloride	5
	No Mn	25
	No Na₂CO₃	84
	K₂CO₃ instead of Na₂CO₃	80
	NaHCO₃ instead of Na₂CO₃	91
	NaOMe instead of Na₂CO₃	N.D.
	DMSO instead of CH₃CN	N.D.
	DMF instead of CH₃CN	53
	Toluene instead of CH₃CN	Trace
	1,4-Dioxane instead of CH₃CN	24
	Fe instead of Mn	32
	MnCl₂ instead of Mn	N.D.
	80 ℃ instead of 130 ℃	Trace

8-氨基喹啉骨架螯合的四配位B,B-二芳基络合物的合成与计算研究

Synthetic and Computational Study of Four-Coordinate B,B-Diaryl 8-Aminoquinolate Complexes

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