University of Illinois Urbana-Champaign

Development of Nickel and Zirconium Mediated Cycloadditions for the Synthesis of Substituted Pentacene

Deaton, Kimberly Rae

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Description

Title
Development of Nickel and Zirconium Mediated Cycloadditions for the Synthesis of Substituted Pentacene
Author(s)
Deaton, Kimberly Rae
Issue Date
2006
Doctoral Committee Chair(s)
Mary S. Gin
Department of Study
Chemistry
Discipline
Chemistry
Degree Granting Institution
University of Illinois at Urbana-Champaign
Degree Name
Ph.D.
Degree Level
Dissertation
Keyword(s)
Chemistry, Organic
Language
eng
Abstract
The regioselectivity of the [2+2+2] cycloaddition of nickel-benzynes and 1,3-diynes could be maintained when asymmetrically substituted 1,3-diynes were employed. The ability to incorporate an asymmetric 1,3-diyne into the oligoacene backbone provided substituents that could be differentiated in subsequent reactions. Conversion of silyl alkynes to bromo alkynes allowed Bergman aromatization of the naphthalenes to occur. The substituted anthracenes formed could then be treated with bis(triphenylphosphine)dichloro-nickel(II) and sodium amalgam to produce a nickelaryne. Application of the [2+2+2] cycloaddition methodology to the longer nickel-aryne in the presence of a 1,3-diyne resulted in an iterative pathway for the synthesis of substituted pentacene. Preliminary efforts for the direct polymerization of poly[n]acene are herein described including the investigation of a possible [4+2] cycloaddition of zirconium-benzyne and 1,3-diynes.
Graduation Semester
2006
Type of Resource
text
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http://hdl.handle.net/2142/84256

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