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

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  • Format: Hardcover
  • Copyright: 2009-08-14
  • Publisher: World Scientific Pub Co Inc
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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

Prefacep. v
Introduction About l,l'-Binaphthylsp. 1
Referencesp. 10
Main Chain Chiral-Conjugated Polymersp. 13
Introduction About Chiral-Conjugated Polymersp. 13
Binaphthyl-Based Polyarylenevinylenesp. 17
Binaphthyl-Based Polyarylenesp. 20
Binaphthyl-Based Polyaryleneethynylenesp. 23
Binaphthyl-Thiophene Copolymersp. 30
Copolymers of BINAM and Thiophene-Containing Conjugated Linkersp. 37
Polybinaphthyls Without Conjugated Linkersp. 39
Propeller-Like Polybinaphthylsp. 51
Dipole-Oriented Propeller-Like Polymersp. 69
Binaphthyl-Based Polysalophensp. 71
Helical Ladder Polybinaphthylsp. 76
Referencesp. 85
Polybinaphthyls in Asymmetric Catalysisp. 87
Introduction about Chiral Polymers in Asymmetric Catalysisp. 87
Synthesis of Major-Groove Poly (BINOL)sp. 89
Application of the Major-Groove Poly (BINOL)s to Catalyze the Mukaiyama Aldol Reactionp. 95
Application of the Major-Groove Poly (BINOL)s to Catalyze the Hetero-Diels-Alder Reactionp. 99
Using the Ti(IV) Complex of the Major-Groove Poly (BINOL) to Catalyze the Diethylzinc Addition to Aldehydesp. 101
Synthesis of the Minor-Groove Poly (BINOL)sp. 102
Application of the Major- and Minor-Groove Poly (BINOL)s to Catalyze the Asymmetric Organozinc Addition to Aldehydesp. 105
Asymmetric Reduction of Prochiral Ketones Catalyzed by the Chiral BINOL Monomer and Polymer Catalystsp. 122
Asymmetric Epoxidation of ,-Unsaturated Ketones Catalyzed by the Minor- and Major-Groove Poly (BINOL)sp. 125
Asymmetric Diels-Alder Reaction Catalyzed by Poly (BINOL)-B (III) Complexesp. 133
1,3-Dipolar Cycloaddition Catalyzed by the Minor- and Major-Groove Poly (BINOL)-A1(III) Complexesp. 136
Asymmetric Michael Addition Catalyzed by the Poly (BINOL)sp. 139
Synthesis and Study of Poly (BINAP)p. 141
Synthesis and Study of a BINOL-BINAP Copolymerp. 146
Referencesp. 150
Asymmetric Catalysis by BINOL and Its Non-polymeric Derivativesp. 151
Introductionp. 151
Asymmetric Alkyne Additions to Aldehydesp. 151
Asymmetric Arylzinc Addition to Aldehydesp. 198
Asymmetric Alkylzinc Addition to Aldehydesp. 216
Asymmetric TMSCN Addition to Aldehydesp. 225
Asymmetric Hetero-Diels-Alder Reactionp. 233
Referencesp. 235
Enantioselective Fluorescent Sensors Based on l,l'-Binaphthyl-Derived Dendrimers, Small Molecules and Macrocyclesp. 239
Introductionp. 239
Using Phenyleneethynylene-BINOL Dendrimers for the Recognition of Amino Alcoholsp. 240
Using Phenylene-BINOL Dendrimers for the Recognition of Chiral Amino Alcoholsp. 246
Using Functionalized BINOLs for the Recognition of Amino Alcohols and Aminesp. 252
Using Acyclic Bisbinaphthyls for the Recognition of -Hydroxycarboxylic Acids and Amino Acid Derivativesp. 257
Using Diphenylethylenediamine-BINOL Macrocycles for the Recognition of -Hydroxycarboxylic Acidsp. 263
Using Cyclohexanediamine-BINOL Macrocycles and Their Derivatives for the Recognition of -Hydroxycarboxylic Acids and Amino Acid Derivativesp. 282
Application of the Cyclohexanediamine-BINOL Macrocycle Sensor in Catalyst Screening31p. 294
Using Monobinaphthyl Compounds for the Recognition of -Hydroxycarboxylic Acids and Amino Acid Derivativesp. 299
Enantioselective Precipitation and Solid-State Fluorescence Enhancement in the Recognition of -Hydroxycarboxylic Acids by Using Monobinaphthyl Compoundsp. 303
Referencesp. 308
Miscellaneous Studies on Materials Related to l,l'-Binaphthylsp. 311
Chiral Molecular Wiresp. 311
A Biphenol Polymerp. 316
Supramolecular Chemistry of Self-Assembly of Racemic and Optically Active Propargylic Alcoholsp. 318
Referencesp. 331
Indexp. 333
Table of Contents provided by Ingram. All Rights Reserved.

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