The Resource In pursuit of extraordinarily twisted acenes, Robert Gene Clevenger

In pursuit of extraordinarily twisted acenes, Robert Gene Clevenger

Label
In pursuit of extraordinarily twisted acenes
Title
In pursuit of extraordinarily twisted acenes
Statement of responsibility
Robert Gene Clevenger
Creator
Contributor
Author
Degree supervisor
Subject
Genre
Language
eng
Summary
Longitudinally twisted acenes are a topologically interesting class of polycyclic aromatic hydrocarbons (PAHs), and it could be argued that they have quite beautiful chemical structures, too. X-ray crystal analysis of many of these acenes has found them to adopt a helical conformation where the axis of propagation runs parallel to their linearly fused benzene rings. The measured end-to-end twists of many of those currently reported range from a modest 28.1° to an extreme of 143.6°. The helical nature of longitudinally twisted acenes implies chirality, and compared to their racemic mixtures, the pure enantiomers display chiroptical properties, which make them interesting for study and potentially useful in materials applications. The deformation in these compounds is induced by the placement of bulky substituents at the peri positions of the acene, adjacent to one another, which forces the acene to twist out of plane in order to alleviate the steric strain. Because of the substitution requirement, longitudinally twisted acenes can be quite challenging synthetic targets. The current and by far most successful synthetic approach to these compounds is by what we refer to as the 2benzyne3 approach, which requires the design of a benzyne precursor and its subsequent trapping by a diene compatible with the reaction conditions necessary to generate the aryne. Although quite successful, this approach suffers from many drawbacks including low overall yields, difficulty in derivatization, and lack of scalability. The focus of the dissertation is the application of an alternative synthetic approach to these compounds, which we found gave good overall yields, allowed for easy derivatization, and could be scaled-up to produce gram quantities if desired. Combining an unusually reactive thiophene with a novel reduction method, we were able to synthesize a diverse number of longitudinally twisted acenes. Among these are included the now most twisted anthracene, the most twisted true pentacene, and the most twisted acene as determined by X-ray crystallography.
Cataloging source
UMK
http://library.link/vocab/creatorDate
1968-
http://library.link/vocab/creatorName
Clevenger, Robert Gene
Degree
Ph.D.
Dissertation note
(Department of Chemistry and Department of Physics and Astronomy).
Dissertation year
2014.
Granting institution
University of Missouri-Kansas City,
Illustrations
illustrations
Index
no index present
Literary form
non fiction
Nature of contents
  • dictionaries
  • bibliography
  • theses
http://library.link/vocab/relatedWorkOrContributorDate
1963-
http://library.link/vocab/relatedWorkOrContributorName
Kilway, Kathleen V.
http://library.link/vocab/subjectName
Polycyclic aromatic hydrocarbons
Label
In pursuit of extraordinarily twisted acenes, Robert Gene Clevenger
Instantiates
Publication
Note
  • "A dissertation in Chemistry and Physics."
  • Advisor: Kathleen V. Kilway
  • Vita
Antecedent source
not applicable
Bibliography note
Includes bibliographical references (pages 313-319)
Carrier category
online resource
Carrier category code
  • cr
Carrier MARC source
rdacarrier
Color
black and white
Content category
text
Content type code
  • txt
Content type MARC source
rdacontent
Contents
Introduction to longitudinally twisted acenes -- The benzyne synthesis of longitudinally twisted acenes derived from a polycyclic thiophene -- An alternative synthetic approach to longitudinally twisted acenes -- Synthesis of exceptionally twisted acenes -- Application of a novel reduction method -- Experimental details and crystal data
Control code
949797022
Dimensions
unknown
Extent
1 online resource (321 pages)
File format
one file format
Form of item
online
Level of compression
mixed
Media category
computer
Media MARC source
rdamedia
Media type code
  • c
Other physical details
illustrations.
Quality assurance targets
not applicable
Specific material designation
remote
System control number
(OCoLC)949797022
System details
  • The full text of the dissertation is available as an Adobe Acrobat .pdf file; Adobe Acrobat Reader required to view the file
  • Mode of access: World Wide Web
Label
In pursuit of extraordinarily twisted acenes, Robert Gene Clevenger
Publication
Note
  • "A dissertation in Chemistry and Physics."
  • Advisor: Kathleen V. Kilway
  • Vita
Antecedent source
not applicable
Bibliography note
Includes bibliographical references (pages 313-319)
Carrier category
online resource
Carrier category code
  • cr
Carrier MARC source
rdacarrier
Color
black and white
Content category
text
Content type code
  • txt
Content type MARC source
rdacontent
Contents
Introduction to longitudinally twisted acenes -- The benzyne synthesis of longitudinally twisted acenes derived from a polycyclic thiophene -- An alternative synthetic approach to longitudinally twisted acenes -- Synthesis of exceptionally twisted acenes -- Application of a novel reduction method -- Experimental details and crystal data
Control code
949797022
Dimensions
unknown
Extent
1 online resource (321 pages)
File format
one file format
Form of item
online
Level of compression
mixed
Media category
computer
Media MARC source
rdamedia
Media type code
  • c
Other physical details
illustrations.
Quality assurance targets
not applicable
Specific material designation
remote
System control number
(OCoLC)949797022
System details
  • The full text of the dissertation is available as an Adobe Acrobat .pdf file; Adobe Acrobat Reader required to view the file
  • Mode of access: World Wide Web

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