Improved synthesis dimethylhomoecoerdianthrone (HOCD) and its functionalization through facile amination reactions

doi:10.1016/j.dyepig.2016.03.016

	Improved synthesis dimethylhomoecoerdianthrone (HOCD) and its functionalization through facile amination reactions
	Wu, Haixia 1; Chen, Wei 1; Yang, Hui 2; Wang, Suhua 3; Lim, Si Ting 1; Yao, Wei 1; Guo, Juanjuan 1; Li, Tianhu 5; Wong, Ming Wah 2; Huang, Dejian 1,4
	2016-07-01
发表期刊	DYES AND PIGMENTS
摘要	An improved synthesis of dimethylhomoecoerdianthrone (HOCD), a dye used for singlet oxygen detection, was reported by isolation of a key intermediate followed by cyclization reaction. Moreover, dehydrogenative amination reaction between HOCD and alkyl amines and diamines resulted in amine functionalized HOCD derivatives with good yield. The observed reactivity depends on the nucleophilicity of amine and electrophilicity of HOCD. DFT calculations suggest that the reaction involves 1,4-Michael addition followed by migration of hydrogen atom due to aromatization. Under the aerated conditions, dehydrogenation occurs to restore the ketone structure. This C-N coupling reaction can be utilized to construct molecular materials with near infrared photonic properties. Finally, we illustrated that the HOCD derives, HOCD-SO3-, can be grafted to semiconductor nanocrystals (quantum dots) to give turn-on fluorescent nanoprobe for highly selective detection of singlet oxygen. (C) 2016 Elsevier Ltd. All rights reserved.
文章类型	Article
关键词	Singlet Oxygen Amination Sulfonation Dimethylhomoecoerdianthrone Dft Calculation Quantum Dots Fluorescent Probe
WOS标题词	Science & Technology ; Physical Sciences ; Technology
DOI	10.1016/j.dyepig.2016.03.016
关键词[WOS]	SINGLET OXYGEN ; PROBE ; TRIPHENYLMETHANE ; SYSTEMS ; OXIDE
收录类别	SCI
语种	英语
项目资助者	Ministry of Education of Singapore(MOE2014-T2-1-134) ; Ministry of Education of Singapore(MOE2014-T2-1-134) ; Ministry of Education of Singapore(MOE2014-T2-1-134) ; Ministry of Education of Singapore(MOE2014-T2-1-134) ; Ministry of Education of Singapore(MOE2014-T2-1-134) ; Ministry of Education of Singapore(MOE2014-T2-1-134) ; Ministry of Education of Singapore(MOE2014-T2-1-134) ; Ministry of Education of Singapore(MOE2014-T2-1-134) ; Natural Science Foundation of Jiangsu Province(R-2014-S-013) ; Natural Science Foundation of Jiangsu Province(R-2014-S-013) ; Natural Science Foundation of Jiangsu Province(R-2014-S-013) ; Natural Science Foundation of Jiangsu Province(R-2014-S-013) ; Natural Science Foundation of Jiangsu Province(R-2014-S-013) ; Natural Science Foundation of Jiangsu Province(R-2014-S-013) ; Natural Science Foundation of Jiangsu Province(R-2014-S-013) ; Natural Science Foundation of Jiangsu Province(R-2014-S-013) ; National Natural Science Foundation of China(21228702) ; National Natural Science Foundation of China(21228702) ; National Natural Science Foundation of China(21228702) ; National Natural Science Foundation of China(21228702) ; National Natural Science Foundation of China(21228702) ; National Natural Science Foundation of China(21228702) ; National Natural Science Foundation of China(21228702) ; National Natural Science Foundation of China(21228702)
WOS研究方向	Chemistry ; Engineering ; Materials Science
WOS类目	Chemistry, Applied ; Engineering, Chemical ; Materials Science, Textiles
WOS记录号	WOS:000377838700018
引用统计	被引频次：7[WOS] [WOS记录] [WOS相关记录]
文献类型	期刊论文
条目标识符	http://ir.hfcas.ac.cn:8080/handle/334002/30865
专题	中科院合肥智能机械研究所
作者单位	1.Natl Univ Singapore, Dept Chem, Food Sci & Technol Programme, Sci Dr 3, Singapore 117543, Singapore 2.Natl Univ Singapore, Dept Chem, Sci Dr 3, Singapore 117543, Singapore 3.Chinese Acad Sci, Inst Intelligent Machines, Hefei 230031, Anhui, Peoples R China 4.Natl Univ Singapore Suzhou, Res Inst, 377 Linquan St, Suzhou 215123, Peoples R China 5.Nanyang Technol Univ, Sch Phys & Math Sci, Div Chem & Biol Chem, SPMS-CBC-04-21,21 Nanyang Link, Singapore 637371, Singapore
推荐引用方式 GB/T 7714	Wu, Haixia,Chen, Wei,Yang, Hui,et al. Improved synthesis dimethylhomoecoerdianthrone (HOCD) and its functionalization through facile amination reactions[J]. DYES AND PIGMENTS,2016,130(无):154-161.
APA	Wu, Haixia.,Chen, Wei.,Yang, Hui.,Wang, Suhua.,Lim, Si Ting.,...&Huang, Dejian.(2016).Improved synthesis dimethylhomoecoerdianthrone (HOCD) and its functionalization through facile amination reactions.DYES AND PIGMENTS,130(无),154-161.
MLA	Wu, Haixia,et al."Improved synthesis dimethylhomoecoerdianthrone (HOCD) and its functionalization through facile amination reactions".DYES AND PIGMENTS 130.无(2016):154-161.

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