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Updated: May 9, 2026
Soft Lithographic Functionalization and Patterning Oxide-free Silicon and Germanium
Published on: December 16, 2011
Organic monolayers from 1-alkynes covalently attached to chromium nitride: alkyl and fluoroalkyl termination
Sidharam P Pujari1, Luc Scheres, Barend van Lagen
1Laboratory of Organic Chemistry, Wageningen University, Dreijenplein 8, 6703 HB Wageningen, The Netherlands.
Abstract:
Strategies to modify chromium nitride (CrN) surfaces are important because of the increasing applications of these materials in various areas such as hybrid electronics, medical implants, diffusion barrier layers, corrosion inhibition, and wettability control. The present work presents the first surface immobilization of alkyl and perfluoro-alkyl (from C6 to C18) chains onto CrN substrates using appropriately functionalized 1-alkynes, yielding covalently bound, high-density organic monolayers with excellent hydrophobic properties and a high degree of short-range order. The obtained monolayers were characterized in detail by water contact angle, X-ray photoelectron spectroscopy (XPS), ellipsometry, and infrared reflection absorption spectroscopy (IRRAS).
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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.
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.
02:47Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation
One of the convenient methods for the preparation of aldehydes and ketones is via hydration of alkynes. Hydroboration-oxidation of alkynes is an indirect hydration reaction in which an alkyne is treated with borane followed by oxidation with alkaline peroxide to form an enol that rapidly converts into an aldehyde or a ketone. Terminal alkynes form aldehydes, whereas internal alkynes give ketones as the final product.
02:39Nomenclature of Alkynes
02:34Preparation of Alkynes: Dehydrohalogenation
Alkynes can be prepared by dehydrohalogenation of vicinal or geminal dihalides in the presence of a strong base like sodium amide in liquid ammonia. The reaction proceeds with the loss of two equivalents of hydrogen halide (HX) via two successive E2 elimination reactions.
02:24Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation
Like alkenes, alkynes can be reduced to alkanes in the presence of transition metal catalysts such as Pt, Pd, or Ni. The reaction involves two sequential syn additions of hydrogen via a cis-alkene intermediate.