ULTRATHIN ORGANIC FILMS

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1 An Introduction to ULTRATHIN ORGANIC FILMS From Langmuir-Blodgett to Self-Assembly Abraham Ulman Corporate Research Laboratories Eastman Kodak Company Rochester, New York Academic Press San Diego New York Boston London Sydney Tokyo Toronto

2 CONTENTS Preface Acknowledgements Suggestions for Further Reading xv xix xxi PART ONE: ANALYTICAL TOOLS Analysis of Film Properties 2 A. Thickness Measurements 2 B. Fourier Transform Infrared Spectroscopy 6 1. Attenuated Total Reflection Spectroscopy 6 2. Grazing-Angle Spectroscopy 12 C. Raman Spectroscopy 18 D. Surface Potential 21 E. Surface Viscosity 29 F. Electron Paramagnetic Resonance 33 G. X-ray Diffraction 35 H. Electron Diffraction 41 I. Neutron Diffraction 44 J. High-Resolution Electron Energy Loss Spectroscopy 45 ix

3 1.2. Analysis of Surface Properties 48 A. Contact Angles and Surface Tension 48 B. Surface Second-Harmonic Generation 58 C. Low-Energy Helium Diffraction 61 D. Optical Microscopy 63 E. Fluorescence Microscopy 64 F. Electron Microscopy Scanning Electron Microscopy Transmission Electron Microscopy 67 G. Scanning Tunneling Microscopy 68 H. Atomic Force Microscopy 72 I. Scanning Ion Conductance Microscopy 73 J. Surface Plasmon Microscopy 74 K. Auger Electron Spectroscopy 77 L. X-ray Photoelectron Spectroscopy 77 M. Surface Ionization Mass Spectroscopy 81 References 83 PART TWO: LANGMUIR-BLODGETT FILMS Preparation Methods 102 A. The Trough 102 B. Experimental Considerations in the Preparation of LB films The Environment The Subphase The Substrate Amphiphiles and Solvents Between Experiments 110 C. What Is the Amphiphile? 111 D. The Pressure-Area Isotherm E. Film Transfer The Meniscus Vertical Deposition Schaefer's Method for the Preparation of LB films 127 F. Monolayers at the Water-Oil Interface Thermal Stability of LB Films 133 A. Order-Disorder Transitions 133 x

4 B. Monolayer Desorption The Structure of Hydrocarbon LB Films 143 A. Structure at the Water-Air Interface 143 B. LB Films on Solid Substrates LB Films of Fluorocarbon Amphiphiles LB Films Containing Ionophores LB Films of Liquid-Crystal Compounds LB Films of Porphyrins and Phthalocyanines 159 A. LB Films of Porphyrins 161 B. LB Films of Phthalocyanines Polymerie LB Films 176 A. Polymerizable LB Films Amphiphiles Containing One or More Double Bonds Diacetylenic Amphiphiles Amphiphiles Containing an Oxirane Group 190 B. LB Films of Preformed Polymers LB Films of Phospholipids Energy Transfer in LB Films 210 References 219 PART THREE: SELF-ASSEMBLED MONOLAYERS Monolayers of Fatty Acids Monolayers of Organosilicon Derivatives 245 A. Self-Assembled Monolayers and Multilayers: Methodology B. Kinetics of Formation of Alkyltrichlorosilane Monolayers C. Stability of Self-Assembled Monolayers Chemical Stability Thermal Stability 255 D. Structural Issues of Self-Assembled Monolayers 256 E. Self-Assembled Monolayers That Contain Aromatic Groups Self-Assembled Monolayers That Contain Phenoxy Groups Self-Assembled Monolayers Containing a Sulfone Group. 266 F. Formation of Multilayers by Self-Assembly Monolayers of Alkanethiols on Gold 279 A. Kinetics of Formation of Monolayers of Alkanethiols on Gold. 281 B. The Effect of Chain Length on Monolayer Formation 283 C. Solvent Effects on Monolayer Formation 286 xi

5 D. The Structure of Alkanethiol Monolayers on Gold 288 E. FTIR Studies of Alkanethiol Monolayers on Gold and Silver Formation of Double Layers on Gold Orthogonal Self-Assembled Monolayers Concluding Remarks 300 References 301 PART FOUR: MODELING OF MONOLAYERS General Considerations 305 A. Energy Minimizations 307 B. Simulations at Finite Temperatures Monte Carlo Simulations Molecular Dynamics Simulations 308 C. The Choice of a Force Field and Calculations of Its Parameters 309 D. Determination of Partial Atomic Charges Molecular Mechanics 313 A. Simple Alkanethiol Monolayers 313 B. Alkanethiol Monolayers Containing a Polar Aromatic Group Dynamics Simulations of Monolayers 318 A. Molecular Dynamics Methodology MD Simulations of LB Films and Lipid Membranes Modeling of Self-Assembled Monolayers 327 B. Brownian Dynamics 330 References 335 PART FIVE: APPLICATIONS OF LB AND SA FILMS Nonlinear Optics 339 A. Background 339 B. Monolayers and Films with Nonlinear Optical Properties Second-Order Effects Third-Order Effects LB Films in Piezoelectric Devices LB Films in Pyroelectric Devices Electrical Properties of Monolayers 367 A. Dielectric Properties and Breakdown 367 B. Conduction through LB Films 368 xii

6 C. Photoinduced Electron Transfer and Photoconductivity Photoinduced Electron Transfer Photovoltaic Effects Photocurrent through LB Films Conduction in the Plane of an LB Film Chromic Effects in LB Films 385 A. Electrochromic LB Films 385 B. Thermochromic LB Films 386 C. Photochromic LB Films LB Films as Semiconductors LB Films in Resist Applications LB Films in Sensors 392 A. Field Effect Devices 392 B. Optical Sensors 394 C. Biosensors Gas Penetration Properties of Monolayers Tribology of LB and SA Films 400 References 402 AUTHOR'S FINAL NOTE 415 INDEX 425 xiii

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