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通过碳-氧键断裂的开环反应为硼代亚酞菁独特地引入化学官能团。

Ring Opening Reactions through C-O Bond Cleavage Uniquely Adding Chemical Functionality to Boron Subphthalocyanine.

作者信息

Bonnier Catherine, Bender Timothy P

机构信息

Department of Chemical Engineering and Applied Chemistry, University of Toronto, 200 College St., Toronto M5S 3E5, ON, Canada.

Department of Materials Science and Engineering, University of Toronto, 184 College St., Toronto M5S 3E4, ON, Canada.

出版信息

Molecules. 2015 Oct 7;20(10):18237-45. doi: 10.3390/molecules201018237.

DOI:10.3390/molecules201018237
PMID:26457699
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC6332161/
Abstract

We are reporting the unexpected reaction between bromo-boron subphthalocyanine (Br-BsubPc) and THF, 1,4-dioxane or γ-butyrolactone that results in the ring opening of the solvent and its addition into the BsubPc moiety. Under heating, the endocyclic C-O bond of the solvent is cleaved and the corresponding bromoalkoxy-BsubPc derivative is obtained. These novel alkoxy-BsubPc derivatives have remaining alkyl-bromides suitable for further functionalization. The alkoxy-BsubPcs maintain the characteristic strongly absorption in visible spectrum and their fluorescence quantum yields.

摘要

我们报道了溴代硼亚酞菁(Br-BsubPc)与四氢呋喃(THF)、1,4-二氧六环或γ-丁内酯之间意外的反应,该反应导致溶剂开环并加成到BsubPc部分。在加热条件下,溶剂的内环C-O键断裂,得到相应的溴代烷氧基-BsubPc衍生物。这些新型的烷氧基-BsubPc衍生物含有可用于进一步官能化的残留烷基溴。烷氧基-BsubPcs在可见光谱中保持其特征性的强吸收以及荧光量子产率。

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J Phys Chem Lett. 2015 Aug 6;6(15):3121-5. doi: 10.1021/acs.jpclett.5b01254. Epub 2015 Jul 28.
2
Energy Level Tuning of Non-Fullerene Acceptors in Organic Solar Cells.有机太阳能电池中非富勒烯受体的能级调控
J Am Chem Soc. 2015 Jul 22;137(28):8991-7. doi: 10.1021/jacs.5b02808. Epub 2015 Jul 10.
3
Evaluating thiophene electron-donor layers for the rapid assessment of boron subphthalocyanines as electron acceptors in organic photovoltaics: solution or vacuum deposition?
评估噻吩电子给体层用于快速评估硼亚酞菁作为有机光伏中电子受体的性能:溶液沉积还是真空沉积?
Chemphyschem. 2015 Apr 27;16(6):1245-50. doi: 10.1002/cphc.201402751. Epub 2015 Mar 12.
4
An insight into the mechanism of the axial ligand exchange reaction in boron subphthalocyanine macrocycles.深入了解硼酞菁大环中轴向配体交换反应的机理。
J Am Chem Soc. 2014 Oct 8;136(40):14289-98. doi: 10.1021/ja508181b. Epub 2014 Sep 29.
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8.4% efficient fullerene-free organic solar cells exploiting long-range exciton energy transfer.利用长程激子能量转移实现 8.4%效率的无富勒烯有机太阳能电池。
Nat Commun. 2014 Mar 7;5:3406. doi: 10.1038/ncomms4406.
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Subphthalocyanines, subporphyrazines, and subporphyrins: singular nonplanar aromatic systems.亚酞菁、亚卟啉嗪和亚卟啉:独特的非平面芳香体系。
Chem Rev. 2014 Feb 26;114(4):2192-277. doi: 10.1021/cr400088w. Epub 2013 Dec 19.
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