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

文献类型：期刊论文

作者Wu, Haixia1; Chen, Wei1; Yang, Hui2; Wang, Suhua3; Lim, Si Ting1; Yao, Wei1; Guo, Juanjuan1; Li, Tianhu5; Wong, Ming Wah2; Huang, Dejian1,4
刊名DYES AND PIGMENTS
出版日期2016-07-01
卷号130期号:无页码:154-161
关键词Singlet Oxygen Amination Sulfonation Dimethylhomoecoerdianthrone Dft Calculation Quantum Dots Fluorescent Probe
DOI10.1016/j.dyepig.2016.03.016
文献子类Article
英文摘要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.
WOS关键词SINGLET OXYGEN ; PROBE ; TRIPHENYLMETHANE ; SYSTEMS ; OXIDE
WOS研究方向Chemistry ; Engineering ; Materials Science
语种英语
WOS记录号WOS:000377838700018
资助机构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) ; 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)
源URL[http://ir.hfcas.ac.cn:8080/handle/334002/30865]  
专题合肥物质科学研究院_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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来源：合肥物质科学研究院

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