1, 1'-Binaphthyl-Based Chiral Materials: Our Journey

by Pu, Lin

• ISBN13: 9781848164116
• ISBN10: 1848164114
• Format: Hardcover
• Copyright: 2009-08-14
• Publisher: World Scientific Pub Co Inc

Summary

Chiral materials have been studied in the Department of Chemistry at the University of Virginia for applications in areas like asymmetric catalysis, enantioselective fluorescent sensing, and optical/electrical materials. Optically active 1,1'-binaphthyl molecules are used to build novel chiral polymers, dendrimers, macrocycles, and acyclic molecules. 1,1'-Binaphthyl molecules are chosen because of their remarkably stable chiral configuration as well as their high asymmetric inductions in many processes. In this book, both the fundamental knowledge about the 1,1'-binaphthyl molecules and The synthesis of the structurally diverse 1,1'-binaphthyl-based materials are described. The applications of these materials in various fields are also discussed. This book will serve as a reference for graduate students as well as other professionals working in the related fields.

Author Biography

Lin Pu was born in 1965 in Xuyong, Sichuan, P.R. China. He received his B.S. degree in chemistry from Sichuan University in 1984. He then obtained the Doering Fellowship (CGP) for graduate study in the U.S. and enrolled in the Department of Chemisty at University of California San Diego in 1985. Under the supervision of Professor Joseph M.O Connor, he obtained his Ph.D. degree in 1990. From January 1991 to November 1992, he studied in Professor Henry Taube's laboratory at Stanford University as a postdoctoral fellow. From November 1992 to August 1994, he joined Professor Robert H.Grubbs's research group at California Institute of Technology to continue his postdoctoral training. In the fall of 1994, he was appointed as an assistant professor in the Department of Chemistry at North Dakota State University. In 1997, he moved to University of Virginia as an associate professor in the Department of Chemistry. He became a professor of chemistry at University of Virginia in 2003. He was appointed as the Changjiang Chair Professor by the Ministry of Education of China in 2005. The research projects in his laboratory focus on the design and synthesis of novel chiral molecules and macromolecules for applications in areas such as enantioselective fluorescent sensors, asymmetric catalysis, and electrical and optical materials.

Table of Contents

Preface	p. v
Introduction About l,l'-Binaphthyls	p. 1
References	p. 10
Main Chain Chiral-Conjugated Polymers	p. 13
Introduction About Chiral-Conjugated Polymers	p. 13
Binaphthyl-Based Polyarylenevinylenes	p. 17
Binaphthyl-Based Polyarylenes	p. 20
Binaphthyl-Based Polyaryleneethynylenes	p. 23
Binaphthyl-Thiophene Copolymers	p. 30
Copolymers of BINAM and Thiophene-Containing Conjugated Linkers	p. 37
Polybinaphthyls Without Conjugated Linkers	p. 39
Propeller-Like Polybinaphthyls	p. 51
Dipole-Oriented Propeller-Like Polymers	p. 69
Binaphthyl-Based Polysalophens	p. 71
Helical Ladder Polybinaphthyls	p. 76
References	p. 85
Polybinaphthyls in Asymmetric Catalysis	p. 87
Introduction about Chiral Polymers in Asymmetric Catalysis	p. 87
Synthesis of Major-Groove Poly (BINOL)s	p. 89
Application of the Major-Groove Poly (BINOL)s to Catalyze the Mukaiyama Aldol Reaction	p. 95
Application of the Major-Groove Poly (BINOL)s to Catalyze the Hetero-Diels-Alder Reaction	p. 99
Using the Ti(IV) Complex of the Major-Groove Poly (BINOL) to Catalyze the Diethylzinc Addition to Aldehydes	p. 101
Synthesis of the Minor-Groove Poly (BINOL)s	p. 102
Application of the Major- and Minor-Groove Poly (BINOL)s to Catalyze the Asymmetric Organozinc Addition to Aldehydes	p. 105
Asymmetric Reduction of Prochiral Ketones Catalyzed by the Chiral BINOL Monomer and Polymer Catalysts	p. 122
Asymmetric Epoxidation of ¿,ß-Unsaturated Ketones Catalyzed by the Minor- and Major-Groove Poly (BINOL)s	p. 125
Asymmetric Diels-Alder Reaction Catalyzed by Poly (BINOL)-B (III) Complexes	p. 133
1,3-Dipolar Cycloaddition Catalyzed by the Minor- and Major-Groove Poly (BINOL)-A1(III) Complexes	p. 136
Asymmetric Michael Addition Catalyzed by the Poly (BINOL)s	p. 139
Synthesis and Study of Poly (BINAP)	p. 141
Synthesis and Study of a BINOL-BINAP Copolymer	p. 146
References	p. 150
Asymmetric Catalysis by BINOL and Its Non-polymeric Derivatives	p. 151
Introduction	p. 151
Asymmetric Alkyne Additions to Aldehydes	p. 151
Asymmetric Arylzinc Addition to Aldehydes	p. 198
Asymmetric Alkylzinc Addition to Aldehydes	p. 216
Asymmetric TMSCN Addition to Aldehydes	p. 225
Asymmetric Hetero-Diels-Alder Reaction	p. 233
References	p. 235
Enantioselective Fluorescent Sensors Based on l,l'-Binaphthyl-Derived Dendrimers, Small Molecules and Macrocycles	p. 239
Introduction	p. 239
Using Phenyleneethynylene-BINOL Dendrimers for the Recognition of Amino Alcohols	p. 240
Using Phenylene-BINOL Dendrimers for the Recognition of Chiral Amino Alcohols	p. 246
Using Functionalized BINOLs for the Recognition of Amino Alcohols and Amines	p. 252
Using Acyclic Bisbinaphthyls for the Recognition of ¿-Hydroxycarboxylic Acids and Amino Acid Derivatives	p. 257
Using Diphenylethylenediamine-BINOL Macrocycles for the Recognition of ¿-Hydroxycarboxylic Acids	p. 263
Using Cyclohexanediamine-BINOL Macrocycles and Their Derivatives for the Recognition of ¿-Hydroxycarboxylic Acids and Amino Acid Derivatives	p. 282
Application of the Cyclohexanediamine-BINOL Macrocycle Sensor in Catalyst Screening31	p. 294
Using Monobinaphthyl Compounds for the Recognition of ¿-Hydroxycarboxylic Acids and Amino Acid Derivatives	p. 299
Enantioselective Precipitation and Solid-State Fluorescence Enhancement in the Recognition of ¿-Hydroxycarboxylic Acids by Using Monobinaphthyl Compounds	p. 303
References	p. 308
Miscellaneous Studies on Materials Related to l,l'-Binaphthyls	p. 311
Chiral Molecular Wires	p. 311
A Biphenol Polymer	p. 316
Supramolecular Chemistry of Self-Assembly of Racemic and Optically Active Propargylic Alcohols	p. 318
References	p. 331
Index	p. 333
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