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TTF Chemistry. Fundamentals and Applications of Tetrathiafulvalene. Edited by Jun-ichi Yamada and Toyonari Sugimoto

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TTF Chemistry
Fundamentals and
Applications of
Edited by Jun-ichi
Yamada and Toyonari Sugimoto.
Springer Verlag,
Heidelberg 2004.
445 pp., hardcover
E 199.95.—ISBN
The “marriage” of TTF with TCNQ in
1973, which gave rise to the first “true”
organic metal, stimulated work on synthesis of new donor compounds related
to tetrathiafulvalene (TTF). A new
interdisciplinary field was opened, in
which chemists, physicists, and material
scientists all play a role in the synthesis
and understanding of how organic compounds can organize to behave as metals
and even superconductors.
The growth of TTF chemistry since
1973 has been enormous, and in the last
few years TTF derivatives have been
used not only as building blocks of
organic conductors, but also as components of molecular machines, organic
magnets, organic field-effect transistors,
electrochemical sensors, and solar cells.
One opens the book with interest in
learning about the chemistry of the TTF
molecule, which in other books has
usually been reviewed from the point
of view of building blocks for conducting
materials, with an emphasis on the
physical properties. Here the reader
does not find an exhaustive review of
the different methods that can be used
to synthesize TTF and its derivatives,
but instead gets an overview of the
enormous growth that TTF chemistry
Angew. Chem. Int. Ed. 2006, 45, 3003 – 3004
has achieved since 1970/1971, when TTF
was synthesized independently by the
groups of Wudl, H/nig, and Coffen. The
high ambitions of chemists to modify the
TTF molecule to achieve different properties and special applications have
provided most of the derivatives found
in this book. They range from molecules
that are symmetric, asymmetric, heteroatom-substituted, halogenated, stableradical-substituted, dimeric (simple,
fused, or cyclophane-type), or oligomeric (linear, macrocyclic, or dendritic),
to TTF-acceptor-linked molecules and
metal complexes bearing TTF ligands.
This multi-author work consists of
four parts containing 17 chapters altogether. Part I (7 chapters) is devoted to
functionalized TTFs, Part II (3 chapters)
to dimeric TTFs, Part III (4 chapters) to
1,3-dithiol-2-ylidene donors, and Part IV
(3 chapters) to applications of TTFs.
Part I presents a very interesting
overview of the many possibilities to
functionalize TTF so that this heterocycle can act in different ways as a
building block for supramolecular architectures. Most of the chapters describe
the methodologies developed to synthesize the different compounds, and the
electronic and supramolecular characteristics that give specific properties.
Special emphasis is placed on the conducting properties of materials derived
from halogenated TTFs (Chapter 3) and
oxygen analogues of TTFs (Chapter 4),
and it is shown that small changes in
TTF-type molecules can lead to completely different structures having
diverse properties. Chapter 6, which
deals with TTFs functionalized with
stable organic free radicals, introduces
switchable spin systems and spin-polarized donors. The use of TTFs as ligands
of metal complexes is a growing field of
research, which has achieved a breakthrough in the form of neutral molecular
metals; this topic is treated in Chapter 7,
which reviews a few examples and gives
Part II is devoted to dimeric TTF
derivatives linked by a s bond and
dimeric conjugated p systems, with or
without heteroatoms, chalcogen atoms,
alkyl chains, etc. These systems are very
interesting because of the fact that they
can display multistage redox behavior
and undergo both intermolecular and
intramolecular electron transfer. The
three chapters of this part cover not
only dimers but also oligomers, cyclophanes, and bis-fused TTFs, quite new
compounds that give rise to very interesting conducting properties.
In Part III we find a comprehensive
review of 1,3-dithiol-2-ylidene donors
with conjugated and heteroquinoid
spacer groups, and also donors with
multiple 1,3-dithiol-2-ylidene units,
including radialenes. Dihydro-TTFs are
the main subject of Chapter 11, which
concentrates on the supramolecular
aspects and physical properties.
The volume is completed by Part IV,
which is devoted to applications of TTFs,
and describes macrocycles, catenanes,
rotaxanes, donor–acceptor assemblies,
as well as polymers and dendritic TTFs.
The possible applications are based on
different aspects, such as nonlinear optical properties, photoinduced electron
transfer for solar cells, switching in
rotaxanes, and host–guest capabilities of
macrocycles. However, only some
selected aspects of the applications of
TTFs are covered, and the highly versatile switching and sensor capabilities of
TTF-based compounds are not treated
with the required wide range and depth.
The few cases of overlap between
chapters can be excused, and do not
adversely affect the reading of the book,
which presents an up-to-date picture of
various aspects of TTF chemistry. The
index is reasonably effective for finding
particular topics in the text, but the
reader would benefit from a list of
abbreviations, which is sadly missed
when one looks at the list of compounds.
As Fred Wudl states in the foreword
to the book, it is clear from this volume
that TTF chemistry is a vibrant and
active part of the organic chemistry
scene. The book is of great interest,
and is strongly recommended, not only
for organic chemists but also for materials scientists engaged in research in the
field, and for others who seek an introduction to the recent advances in TTF
science as an entry into the truly
dynamic field of molecular electronics.
Concepci Rovira
Institut de Ci+ncia de Materials
de Barcelona (CSIC)
Bellaterra (Spain)
DOI: 10.1002/anie.200485301
0 2006 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
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chemistry, sugimoto, jun, tetrathiafulvalene, application, ttf, edited, ichi, yamada, fundamentals, toyonari
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