Supramolecular Chirality

by Crego-calama, Mercedes; Reinhoudt, David N.; Amabilino, D. B. (CON); Borovkov, V. V. (CON); Ernst, K. H. (CON)

• ISBN13: 9783540321514
• ISBN10: 3540321519
• Edition: 1st
• Format: Hardcover
• Copyright: 2006-06-15
• Publisher: Springer Verlag

Summary

Univ. of Twente, The Netherlands. Topics include chiral spaces in supramolecular assemblies; dynamic helical structures; supramolecular chirogenesis in host-guest systems containing porphyrinoids; supramolecular chirality in coordination chemistry; dynamic chirality; supramolecular chirality; and more. For researchers.

Table of Contents

Chiral Spaces in Supramolecular Assemblies	1	(46)
A. Scarso
J. Rebek, Jr.
Introduction: Chiral Spaces in Supramolecular Assemblies	3	(7)
Kinds and Strength of Weak Intermolecular Forces. Multivalency and Cooperativity Concepts	4	(2)
Lifetime of Supramolecular Assemblies	6	(1)
Examples in Nature	7	(1)
Supramolecular Chirality in Artificial Systems	8	(2)
Chiral Assemblies Comprising Enantiopure Building Blocks	10	(18)
Achiral tris-Melamine with Chiral Cyanurate Assembly	10	(1)
Double Rosettes	11	(1)
Diastereoselective Non-Covalent Synthesis of Chiral Dimelamines---Barbituric Acid Assemblies	11	(3)
Chiral Amplification in Dimelamines-Cyanurate Assemblies	14	(2)
Capsules	16	(1)
Calix[4]arene Urea Dimeric Capsules	16	(3)
Peptido Calix[4]arene Capsules	19	(1)
Ion Pairing Dimeric Capsules	20	(1)
Tetrameric Capsule	21	(2)
Cylindrical Dimeric Capsule	23	(2)
G-Quadruplex Assemblies	25	(1)
Other Dimeric Assemblies	25	(3)
Chiral Assemblies Comprising Achiral Building Blocks	28	(7)
Racemic Capsules	29	(1)
Calix[4]arene Capsules	29	(1)
Tennis Ball Capsule	30	(1)
Softball Capsule	31	(4)
Enantioselective Synthesis via the Chiral Memory Effect	35	(3)
Enantiopure Double Rosettes	35	(2)
Chiral Enantioenriched Softball	37	(1)
Asymmetric Spaces within an Achiral Cylindrical Host	38	(6)
Single Encapsulation	39	(1)
Double Coencapsulation	40	(3)
Triple Coencapsulation	43	(1)
Conclusions	44	(1)
Outlook	44	(3)
References	44	(3)
Dynamic Helical Structures: Detection and Amplification of Chirality	47	(42)
K. Maeda
E. Yashima
Introduction	48	(1)
Helical Aggregates	49	(12)
Helical Aggregates Based on Small Molecules	49	(6)
Chiral Amplification by Helical Aggregates	55	(5)
Chirality Sensing by Helical Aggregates	60	(1)
Helical Macromolecules and Oligomers	61	(19)
Poly(phenylacetylene)s	62	(5)
Other Helical Polymers and Oligomers	67	(4)
Chirality Sensing by Helix Inversion	71	(3)
Memory and Storage of Helical Chirality	74	(4)
Chirality Sensing in Gel and Solid	78	(1)
Sensing and Amplification of Chirality in Liquid Crystal	79	(1)
Supramolecular Assembly of Helical Polymers	80	(3)
Conclusion	83	(6)
References	84	(5)
Supramolecular Chirogenesis in Host-Guest Systems Containing Porphyrinoids	89	(58)
V. V. Borovkov
Y. Inoue
Introduction	90	(3)
Supramolecular Chirogenesis: Definition, Significance, and Occurrence in Natural Systems	90	(1)
Overview of Latest Reviews	91	(2)
Supramolecular Systems on the Basis of Monomeric Porphyrinoids	93	(6)
Achiral/Racemic Porphyrinoids	93	(4)
Chiral Porphyrinoids	97	(2)
Chiral Dimeric/Oligomeric Porphyrinoids Constructed from Achiral Monomers Fixed by Noncovalent Bridges	99	(6)
Supramolecular Systems on the Basis of Dimeric/Oligomeric Porphyrinoids	105	(21)
Achiral/Racemic Porphyrinoids	105	(12)
Chiral Porphyrinoids	117	(1)
Interactions with Achiral Counterparts	118	(3)
Interactions with Chiral Counterparts	121	(5)
Supramolecular Systems on the Basis of Aggregated Porphyrinoids	126	(15)
Monomeric Achiral/Racemic Porphyrinoids	126	(1)
Spontaneous Resolution and Stirring Induced Chirality	126	(3)
Interactions with Chiral Counterparts	129	(2)
Monomeric Chiral Porphyrinoids	131	(8)
Dimeric/Oligomeric Porphyrinoids	139	(2)
Concluding Remarks and Future Perspectives	141	(6)
References	142	(5)
Supramolecular Chirality in Coordination Chemistry	147	(38)
G. Seeber
B. E. F. Tidemann
K. N. Raymond
Introduction	148	(11)
Generation of Chirality	152	(1)
Overview of Coordination Assemblies	153	(2)
Racemization of Coordination Assemblies	155	(4)
Chiral Supramolecular Architectures	159	(19)
Helicates	159	(1)
Single-Stranded Helicates	159	(1)
Double-Stranded Helicates	160	(1)
Triple-Stranded Helicates	160	(1)
Quadruple-Stranded Helicates	161	(1)
Circular Helicates	162	(1)
Trigonal (Anti)prism	162	(4)
Tetrahedra	166	(1)
M4L6 Stoichiometry	166	(5)
M4L4 Stoichiometry	171	(2)
M6L4 Stoichiometry	173	(2)
Trigonal Bipyramid	175	(1)
Octahedra	175	(1)
Cuboctahedra	176	(2)
Conclusions and Outlook	178	(7)
References	179	(6)
Dynamic Chirality: Molecular Shuttles and Motors	185	(24)
D. A. Leigh
E. M. Perez
Introduction	185	(2)
Controlled Motion at the Molecular Level; Walking in a Hurricane	186	(1)
Dynamic Chirality in Covalently Linked Molecular Rotors	187	(8)
Dynamic Chirality in Interlocked Architectures	195	(11)
Translational Isomerism in Molecular Shuttles	196	(2)
Translational Isomerism in Catenanes	198	(6)
Influencing the Expression of Chirality with Interlocked Architectures	204	(2)
Conclusions and Outlook	206	(3)
References	206	(3)
Supramolecular Surface Chirality	209	(44)
K.-H. Ernst
Introduction	211	(8)
Chirality at Surfaces	211	(2)
Structures of Clean Surfaces	213	(2)
Experimental Aspects	215	(1)
Molecular Deposition	216	(1)
STM	216	(2)
LEED	218	(1)
Achiral Molecules at Surfaces	219	(7)
Surface-Induced Chirality	219	(2)
Molecular Rearrangement	221	(1)
Reaction-Induced Chirality	222	(1)
Assembly-Enforced Chirality	223	(1)
Substrate Lattice-Induced Chirality	224	(2)
Chiral Recognition in Two Dimensions	226	(19)
Enantiomorphism at Surfaces	226	(1)
Chiral Patterns in Close-Packed Monolayers	227	(4)
Chiral Clusters, Chains and Rings	231	(3)
Losing the Expression: Achiral Lattices from Chiral Molecules	234	(2)
Spontaneous Resolution	236	(7)
Enantiospecific Surface Chemistry	243	(1)
Diastereoisomeric Recognition	244	(1)
Amplification of Chirality in Two Dimensions	245	(4)
Homochirality from Prochiral Precursors	245	(1)
Homochiral Pseudo-Racemic Systems	246	(2)
Magnetic Field Induced Enantiomeric Excess	248	(1)
Outlook	249	(4)
References	249	(4)
Supramolecular Chiral Functional Materials	253	(50)
D. B. Amabilino
J. Veciana
Introduction	254	(1)
Why Chiral Functional Materials?	254	(1)
Preparing Supramolecular Chiral Materials	254	(1)
Supramolecular Chirality in Systems of Interest in Molecular Electronics	255	(8)
Conductivity in Materials	255	(1)
Chiral Conductors Incorporating Small Molecules	256	(3)
Chiral Polymeric Conductors	259	(4)
Stereochemistry of Supramolecular Liquid Crystals	263	(14)
Intrinsically Chiral Supramolecular Liquid Crystals	264	(5)
Induced Chirality in Achiral Liquid Crystals	269	(5)
Spontaneous Resolution in Achiral and Racemic Liquid Crystals	274	(3)
Gels	277	(4)
Chiral Magnets	281	(7)
Materials with Interesting Optical Properties	288	(6)
Colourants	288	(4)
Nonlinear Optical Materials	292	(1)
Luminescent Materials	293	(1)
Conclusion and Outlook	294	(9)
References	294	(9)
Author Index Volumes 251--265	303	(8)
Subject Index	311