J. Joule – Thiophenes (2015)

Автор: J. Joule
Название книги: Thiophenes (2015)
Формат: PDF
Жанр: Химия
Страницы: 303
Качество: Изначально компьютерное, E-book

The series Topics in Heterocyclic Chemistry presents critical reviews on present and future trends in the research of heterocyclic compounds. Overall the scope is to cover topics dealing with all areas within heterocyclic chemistry, both experimental and theoretical, of interest to the general heterocyclic chemistry community. The series consists of topic related volumes edited by renowned editors with contributions of experts in the field.

Thiophene was first recognised by the German chemist Viktor Meyer, then at
Zurich, as an ‘impurity’ in the commercial (coal tar) benzene available in the
nineteenth century. His isolation of the substance in the 1880s began investigations
of this benzene-like aromatic heterocycle, which have continued to the present.
Especially important were the extensive investigations by Salo Gronowitz at Lund
University, Sweden. Thus, the chemistry of the five-membered aromatic
heterocyclc thiophene is well developed, but still remains a very active area of
interest in several contexts. In this book we have sought to both summarise the
important chemical reactivities of thiophenes and illustrate the role of thiophene
chemistry in the development of electroactive materials.
A short, general introductory chapter describes the aromatic structure of thiophene,
C4H4S, placing it in the same family of heterocycles as pyrrole and furan.
We deal with the principal routes for the ring synthesis of thiophenes from
precursors which do not contain the nucleus (chapter “De Novo Ring Synthesis
of Thiophenes”). This is followed by a discussion of the substitution of thiophenes
with electrophilic, nucleophilic and radical reagents (chapter “Thiophene Substitution
Chemistry”), and of the metallation of thiophenes, by various means, and the
reactivity of the metallated species as nucleophiles and as participants in transition
metal-catalysed cross-coupling reactions (chapter “Thiophene Metallation and
Cross-Coupling Chemistry”). With this fundamental reactivity background, the
book goes on to discuss the application of this knowledge for the synthesis of
fused thiophenes (containing two or more thiophene rings) (chapter “Fused
Thiophenes and Some Oligomers and Polymers Therefrom”) that are of relevance
to the construction of organic light emitting diodes, organic field effect transistors,
dye sensitized solar cells and electrochromic devices. Chapter “Thiophene in
Conducting Polymers: Synthesis of Poly(thiophene)s and Other Conjugated
Polymers Containing Thiophenes, for Application in Polymer Solar Cells” shows
how thiophenes are incorporated into conducting polymers with applications as
light absorbing materials in polymer solar cells. The book is completed with a
discussion of S-oxidation of thiophenes and the reactions of the resulting thiophene S-oxides and S,S-dioxides, and the reduction of thiophenes, showing how each of
these aspects of thiophene chemistry can lead to the construction of other, quite
structurally different types of compound (chapter “Thiophene Oxidation and
Reduction Chemistry”).
I am greatly indebted to my authors for their outstanding contributions to this
timely summary of thiophene chemistry. I thank Tanja Jaeger and the Springer staff
in Germany who made the administrative aspects of preparing this volume straightforward,
especially Elizabeth Hawkins for her calming and constructive advice, and
the colleagues in India, especially Arun Manoj Jayaraman. Finally, I particularly
wish to record my thanks to Bert Maes for the invitation to act as Editor of this
volume in the Springer “Topics in Heterocyclic Chemistry” series.