- Functionalized carbon nanohoops: Synthesis and structure of a [9]cycloparaphenylene bearing three 5,8-dimethoxynaphth-1,4-diyl units
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A functionalized [9]cycloparaphenylene ([9]CPP) bearing three evenly spaced 5,8-dimethoxynaphth-1,4-diyl units and two macrocyclic [6]CPP precursors have been synthesized. The Diels-Alder reaction between (E,E)-1,4-bis(4-bromophenyl)- 1,3-butadiene and 1,4-benzoquinone followed by methylation produces cis-5,8-bis(4-bromophenyl)-5,8-dihydro-1,4-dimethoxynaphthalene as the key intermediate for the construction of the hooplike structures. The nickel-mediated homocoupling reactions followed by aromatization led to the functionalized [9]CPP.
- Huang, Changfeng,Huang, Yiwei,Akhmedov, Novruz G.,Popp, Brian V.,Petersen, Jeffrey L.,Wang, Kung K.
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- Formation of Functional Cyclooctadiene Derivatives by Supramolecularly- Controlled Topochemical Reactions and Their Use as Highly Selective Fluorescent Biomolecule Probes?
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Controlling the regio- and stereochemistry of the photoproducts in solution is far more challenging for polyenes than for monoalkenes. Herein, a supramolecularly-controlled topochemical reaction of conjugated dienes in homogeneous system is developed, ultimately providing two cyclooctadiene-cored tetraimidazolium molecular receptors exclusively. These cyclooctadiene derivatives exhibited highly sensitive and selective fluorescence sensing for thymine relative to other biologically relevant species in aqueous solution at physiological pH. Both the cyclooctadiene moieties and imidazolium units play important roles in the selective recognition observed. The presented supramolecularly-controlled method allows the simple yet rare selective photoconversion of flexible cyclooctadiene derivatives in solution. This study offers a new synthetic strategy for the preparation of functional molecules with potential for use in biological applications.
- Gan, Ming-Ming,Han, Ying-Feng
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- Selective dimerization of aryl-substituted terminal alkynes on bis(indenyl)zirconocene derivatives
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Dimerization of aryl-substituted terminal alkynes on indenyl zirconium complexes occurred in a selective way. 1,4-Aryl-1,3-diene derivatives were formed exclusively after hydrolysis. It is in sharp contrast to the reaction on [Cp2Zr] complexes.
- Ren, Shenyong,Seki, Takashi,Necas, David,Shimizu, Hiroyuki,Nakajima, Kiyohiko,Kanno, Ken-Ichiro,Song, Zhiying,Takahashi, Tamotsu
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supporting information
p. 1443 - 1444
(2013/05/21)
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- Synthesis of p-Quinquephenyl from E,E-1,4-Bis(4-bromophenyl)-1,3-butadiene
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p-Quinquephenyl was synthesized in five steps from E,E-1,4-bis(4- bromophenyl)-1,3-butadiene in 34% overall yield. The butadiene was prepared in six steps from 4-bromobenzaldehyde in 35% overall yield. Copyright Taylor & Francis Group, LLC.
- Davis, Matthew C.,Groshens, Thomas J.
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p. 206 - 218
(2011/03/18)
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- Palladium-catalyzed oxidative homocoupling of potassium alkenyltrifluoroborates: synthesis of symmetrical 1,3-dienes
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Herein, we describe a convenient method for the synthesis of symmetrical 1,3-dienes employing an oxidative palladium-catalyzed homocoupling of potassium alkenyltrifluoroborates providing products in good yields relative to existing methodologies. This is the first report of a cross-dimerization of potassium alkenyltrifluoroborates.
- Weber, Minéia,Singh, Fateh V.,Vieira, Adriano S.,Stefani, Hélio A.,Paix?o, Marcio W.
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experimental part
p. 4324 - 4327
(2009/10/26)
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