Design of Organic Solids

220 Pages·1998·5.52 MB·English

by  Jenny P. Glusker (auth.), Y. Aoyama, G. R. Desiraju, J. P. Glusker, R. E. Meléndez

198
Topics in Current Chemistry
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A. de Meijere � K.N. H o u k . H. Kessler
J.-M. L e h n . $.V. Ley . S.L. Schre iber � J. T h i e m
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Design of Organic Solids
Volume Editor: E. Weber
With contributions by"
Y. Aoyama, M. R. Caira, G. R. Desiraju, J. P. Glusker,
A.D. Hamilton, R. E. Mel~ndez, A. Nangia
~ Springer
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ISSN 0340-1022
ISBN 3-540-64645-0
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Institut for Organische Chemie
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Preface
Considering the high level of our knowledge concerning covalent bond
formation in the organic chemistry of molecules, our understanding of the
principles involved in organic solid design is almost in its infancy. While
chemists today are able to synthesize organic molecules of very high complexity
using sophisticated methods of preparation, they lack general approaches
enabling them to reliably predict organic crystalline or solid structures from
molecular descriptors - no matter how simple they are. On the other hand,
nearly all the organic matter surrounding us is not in the single-molecule state
but aggregated and condensed to form liquid or solid molecular assemblages
and structural arrays giving rise to the appearances and properties of organic
compounds we usually observe. Obviously, the electrical, optical or magnetic
properties of solid organic materials that are important requirements for future
technologies and high-tech applications, as well as the stability and solubility
behavior of a medicament depend on the structure of the molecule and the
intramolecular forces, but even more decisively on the intermolecular forces, i. e.
the packing structure of the molecules to which a general approach is lacking.
This situation concerned ]. Maddox some years ago to such a degree that he
described it as "one of the continuing scandals in the physical sciences" [see
(1998) Nature 335:201; see also Ball, P. (1996) Nature 381:648].
The problem of predicting organic solid and crystal structures is very diffi-
cult. The solid state and crystalline arrangements adopted by organic molecules
depend on a subtle balance of intermolecular interactions which can be
achieved for a given conformation in a particular packing arrangement giving
rise to what is called polymorphism. Any approach to using theoretical methods
to help predict organic crystalline and solid structures must therefore take into
account this problematic balance between the intra- and intermolecular inter-
action energies present - strictly speaking, a point currently unsolvable.
Nevertheless, with the beginning of the supramolecular concepts in chemi-
stry [see (1993) Top. Curr. Chem. Vol. 165 and (1995) Top. Curr. Chem. Vol. 175]
about 25 years ago the situation has continued to improve little by little. In
keeping with the new way of thinking in supramolecular dimensions, i. e. beyond
the molecule, structural chemists and crystallographers have had little difficulty
in recognizing a molecular crystal as the supermolecule par excellence and an
organic solid not just as a collection of molecules but as a defined network struc-
ture. Indeed, the crystallization or solid formation process itself is an impressive
display of supramolecular self-assembly, involving specific molecular recogni-
VIII preface
tion at an amazing level of precision. Taking up the words of one of the authors
(G. R. Desiraju), crystals and solids constitute one end of the supramolecular
continuum and may be viewed as "hard" supermolecules in contrast to the
"softer" supramolecular aggregates which exist in solution. Consequently,
supramolecular chemistry today encompasses the study of molecular crystals
with all the applications and ramifications that such a study implies in the field
of solid-state chemistry, crystal-engineering and materials science both from
organic and inorganic viewpoints.
Many of the prerequisites for such an improved understanding of solid-state
supramolecular chemistry but being focused on organic or essentially organic
solids and their potential design are discussed in the present book, beginning in
the contribution of J. P. Glusker (Chapter 1) in which she considers the directional
aspects ofintermolecular interactions and the directional preferences of binding
of functional groups. In Chapter 2, A. Nangia and G. R. Desiraju attempt to show
the importance of pattern recognition using supramolecular synthons in organic
crystal-engineering and referring also to the implications of such ideas in
related areas. R. E. Mel~ndez and A. D. Hamilton, in Chapter 3, take up this topic
in a more specific way and present advances in this field, directing their focus on
the design of organic solid structures based on the hydrogen-bonded tape,
ribbon and sheet motifs involving complementary intermolecular interactions.
There is much current interest in organic hosts, whose guest binding properties
are reminescent of traditional inorganic zeolites but are composed of organic
and metal-ion building blocks to form controlled solid network structures by
making use of directional interactions such as hydrogen bonding and coordina-
tion. The present stage of these organic zeolite analogs and prospects associated
therewith are discussed from both static and dynamic viewpoints in Chapter 4
by Y. Aoyama. In the closing report of M. R. Caira (Chapter 5), a summary of the
thermodynamic, kinetic and structural considerations of crystalline poly-
morphism which is encountered in all areas of research involving organic solid
substances, giving rise to unique difficulties in solid materials design with facing
of current facts, is presented.
I hope that this book will stimulate new work on the design of organic solids
which is a truly promising topic relating to many important areas of research
and industry. To conclude these words of introduction, I wish to express my
heartfelt appreciation to all the contributors who have made this book possible.
Edwin Weber Freiberg, July 1998
Contents
Directional Aspects of Intermolecular Interactions
J. P. Glusker . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
Supramolecular Synthons and Pattern Recognition
A. Nangia, G. R. Desiraju . . . . . . . . . . . . . . . . . . . . . . . . . . . 57
Hydrogen-Bonded Ribbons , Tapes and Sheets as Motifs
for Crystal Eng inee r ing
R. E. Mel~ndez, A. D. Hami l ton . . . . . . . . . . . . . . . . . . . . . . . . 97
Functional Organic Zeolite Analogues
Y. Aoyama . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 131
Crystalline Polymorphism of Organic Compounds
M. R. Caira . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 163
Author Index Volumes 151 - 198 . . . . . . . . . . . . . . . . . . . . . . 209
Contents of Volume 196
Carbon Rich Compounds I
Volume Editor: A. de Meijere
ISBN 3-540-64110-6
Design of Novel Aromatics Using the Loschmidt Replacement on Graphs
Y. Sritana-Anant, T.J. Seiders, J. S. Siegel
Modern Routes to Extended Aromatic Compounds
S. Hagen, H. Hopf
Carbon Rich Cyclophanes with Unusual Properties - an Update
B. K6nig
Unsaturated Oligoquinanes and Related Systems
R. Haag, A. de Meijere
The Centropolyindanes and Related Centro-Fused Polycyclic
Organic Compounds
D. Kuck
Contents of Volume 197
Dendrimers
Volume Editor: F. V6gtle
ISBN 3-540-64112-1
Iterative Synthesis in Organic Chemistry
N. Feuerbacher, F. V6gtle
Supramolecular Chemistry Within Dendritic Structures
V. V. Narayanan, G. R. Newkome
Divergent Approaches to Phosphorus-Containing Dendrimers
and Their Functionalization
J.-P. Majoral, A.-M. Caminade
Chiral Dendrimers
D. Seebach, P. B. Rheiner, G. Greiveldinger, T. Butz, H. Sellner
Dendrimers with Polymeric Core: Towards Nanocylinders
A.-D. Schl~iter
Electrochemical and Photochemical Properties
of Metal-Containing Dendrimers
M. Venturi, S. Serroni, A. Juris, S. Campagna, V. Balzani
Directional Aspects of Intermolecular Interactions
Jenny P. Glusker
The Institute for Cancer Research, The Fox Chase Cancer Center, 7701 Burholme Avenue,
Philadelphia, PA 19111, USA. E-mail: