Book contents
- Frontmatter
- Contents
- Preface
- Acknowledgements
- List of symbols and units
- List of abbreviations and acronyms
- 1 Introduction to electrochromism
- 2 A brief history of electrochromism
- 3 Electrochemical background
- 4 Optical effects and quantification of colour
- 5 Kinetics of electrochromic operation
- 6 Metal oxides
- 7 Electrochromism within metal coordination complexes
- 8 Electrochromism by intervalence charge-transfer coloration: metal hexacyanometallates
- 9 Miscellaneous inorganic electrochromes
- 10 Conjugated conducting polymers
- 11 The viologens
- 12 Miscellaneous organic electrochromes
- 13 Applications of electrochromic devices
- 14 Fundamentals of device construction
- 15 Photoelectrochromism
- 16 Device durability
- Index
- Plate Section
- References
11 - The viologens
Published online by Cambridge University Press: 10 August 2009
Book contents
- Frontmatter
- Contents
- Preface
- Acknowledgements
- List of symbols and units
- List of abbreviations and acronyms
- 1 Introduction to electrochromism
- 2 A brief history of electrochromism
- 3 Electrochemical background
- 4 Optical effects and quantification of colour
- 5 Kinetics of electrochromic operation
- 6 Metal oxides
- 7 Electrochromism within metal coordination complexes
- 8 Electrochromism by intervalence charge-transfer coloration: metal hexacyanometallates
- 9 Miscellaneous inorganic electrochromes
- 10 Conjugated conducting polymers
- 11 The viologens
- 12 Miscellaneous organic electrochromes
- 13 Applications of electrochromic devices
- 14 Fundamentals of device construction
- 15 Photoelectrochromism
- 16 Device durability
- Index
- Plate Section
- References
Summary
Introduction
The next major group of electrochromes are the bipyridilium species formed by the diquaternisation of 4,4′-bipyridyl to form 1,1′-disubstituted-4,4′-bipyridilium salts (Scheme 11.1). The positive charge shown localised on N is better viewed as being delocalised over the rings. The compounds are formally named as 1,1′-di-substituent-4,4′-bipyridilium if the two substituents at nitrogen are the same, and as 1-substitituent-1′-substituent′-4,4′-bipyridilium should they differ. The anion X− in Scheme 11.1 need not be monovalent and can be part of a polymer. The molecules are zwitterionic (i.e. bearing plus and minus charge concentrations at different molecular regions or sites) when a substituent at one nitrogen bears a negative charge.
A convenient abbreviation for any bipyridyl unit regardless of its redox state is ‘bipm’, with its charge indicated. The literature of these compounds contains several trivial names. The most common is ‘viologen’ following Michaelis, who noted the violet colour formed when 1,1′-dimethyl-4,4′-bipyridilium undergoes a one-electron reduction to form a radical cation. 1,1′-Dimethyl-4,4′-bipyridilium is therefore called ‘methyl viologen’ (MV) in this nomenclature. Another extensively used name is ‘paraquat’, PQ, after the ICI brand name for methyl viologen, which they developed for herbicidal use. In this latter style, bipyridilium species other than the dimethyl are called ‘substituent paraquat’.
There are several reviews of this field extant. The most substantial is The Viologens: Physicochemical Properties, Synthesis, and Applications of the Salts of 4,4′-Bipyridine (1998) by Monk.
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- Information
- Electrochromism and Electrochromic Devices , pp. 341 - 373Publisher: Cambridge University PressPrint publication year: 2007
References
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