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Architecture and Electrochemical Performance of Alkynyl-Linked Naphthyl Carbon Skeleton: Naphyne
Yingjie Li1, Yangyang Li2, Peng Lin2
1Anhui Key Lab of Coal Clean Conversion and Utilization, School of Chemistry and Chemical Engineering, Anhui University of Technology, Maanshan 243032, P.R. China.
Abstract:
The synthesis of new sp-hybridized carbon allotropes is a meaningful and challenging issue. Among the alkynyl carbon family, polyaromatic alkynes is a new branch to be developed. Herein, naphyne with a frame construction of alkynyl-linked naphthyl skeleton was efficiently fabricated through targeted mechanochemical reaction of calcium carbide and perchloronaphthalene. Its unique property and structure with wide alkynyl-naphthyl conjugation, multilayered nanofilm morphology, and high structural stability were corroborated by the comprehensive characterizations combined with computational simulations. Because of these structural features, the as-prepared naphyne can be applied as high-performance binder-free supercapacitor electrode with high specific capacitance (154 F g-1), robust long-term retention (92.1% after 5000 cycles), and prominent electrical conductivity (1490 S m-1). The successful architecture of naphyne approves the feasible synthesis of polyaromatic alkynes and further may provide a prospective approach for the development of alkynyl carbon materials.
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02:37Structure and Physical Properties of Alkynes
In nature, compounds containing both carbon and hydrogen are known as "hydrocarbons". Aliphatic hydrocarbons are compounds whose molecules contain saturated single bonds (i.e., alkanes) or unsaturated double or triple bonds. Alkenes contain carbon–carbon double bonds and have a structural formula CnH2n. Unsaturated hydrocarbons containing carbon–carbon triple bonds are called "alkynes" and are structurally represented by the formula CnH2n-2.
The...
02:39Nomenclature of Alkynes
01:18Aromatic Hydrocarbon Anions: Structural Overview
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02:38Electrophilic Addition to Alkynes: Halogenation
Halogenation is another class of electrophilic addition reactions where a halogen molecule gets added across a π bond. In alkynes, the presence of two π bonds allows for the addition of two equivalents of halogens (bromine or chlorine). The addition of the first halogen molecule forms a trans-dihaloalkene as the major product and the cis isomer as the minor product. Subsequent addition of the second equivalent yields the tetrahalide.
02:42Acidity of 1-Alkynes
The acidic strength of hydrocarbons follows the order: Alkynes > Alkenes > Alkanes. The strength of an acid is commonly expressed in units of pKa — the lower the pKa, the stronger the acid. Among the hydrocarbons, terminal alkynes have lower pKa values and are, therefore, more acidic. For example, the pKa values for ethane, ethene, and acetylene are 51, 44, and 25, respectively, as shown here.
02:27Preparation of Alkynes: Alkylation Reaction
Alkylation of terminal alkynes with primary alkyl halides in the presence of a strong base like sodium amide is one of the common methods for the synthesis of longer carbon-chain alkynes. For example, treatment of 1-propyne with sodium amide followed by reaction with ethyl bromide yields 2-pentyne.