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 Functional
Molecular Materials
 Functional
Molecular Materials
An Introductory Textbook

Matteo Atzori | Flavia Artizzu

Published by
Pan Stanford Publishing Pte. Ltd.
Penthouse Level, Suntec Tower 3
8 Temasek Boulevard
Singapore 038988

Email: [email protected]
Web: www.panstanford.com

British Library Cataloguing-in-Publication Data

A catalogue record for this book is available from the British Library.

Functional Molecular Materials: An Introductory Textbook

Copyright © 2018 by Pan Stanford Publishing Pte. Ltd.
All rights reserved. This book, or parts thereof, may not be reproduced in any form
or by any means, electronic or mechanical, including photocopying, recording
or any information storage and retrieval system now known or to be invented,
without written permission from the publisher.

For photocopying of material in this volume, please pay a copying fee through
the Copyright Clearance Center, Inc., 222 Rosewood Drive, Danvers, MA 01923,
USA. In this case permission to photocopy is not required from the publisher.

ISBN 978-981-4774-76-5 (Hardcover)

ISBN 978-1-351-23366-8 (eBook)
 Contents

Preface xi

1. Introduction to Molecular Materials 1

1.1 What Are Molecular Materials? 1
1.2 The Versatility of Molecular Chemistry 4
1.3 Top-Down and Bottom-Up Approaches 4
1.4 Dimensions and Dimensionalities 6
1.5 A Guide to Design Functional Molecular Materials 7

2. Background 11
2.1 Basic Concepts of Magnetism,
Magnetochemistry, and Molecular Magnetism 11
2.1.1 Magnetic Field 12
2.1.2 Magnetic Induction 13
2.1.3 Magnetic Moment 13
2.1.4 Effect of Magnetic Field on Matter 15
2.1.4.1 Magnetization 15
2.1.4.2 Magnetic permeability and
susceptibility 16
2.1.5 Electronic Magnetic Moments 18
2.1.5.1 Classical model of magnetic
moments 18
2.1.5.2 Quantum mechanical model
of magnetic moments 20
2.1.6 Magnetic Properties of Free Atoms 22
2.1.6.1 Hund’s rules: Occupancy of
available electronic states
(Russell–Saunders scheme) 24
2.1.6.2 Quenching of the orbital
angular momentum L 25
2.1.7 The Curie Law 28
2.1.8 The Curie–Weiss Law 30
2.1.9 Deviations from the Curie Law 32
2.1.10 Effective Magnetic Moment and χT Value 34
2.1.11 Field Dependence of Magnetization 36
vi Contents

2.1.12 Magnetic Exchange Coupling 38

2.1.13 Magnetic Exchange Coupling in a
Dinuclear Compound 41
2.1.14 Multicenter Magnetic Systems and
Spin Hamiltonian Approach 44
2.2 Transport Properties of Molecular Materials 46
2.2.1 Electrical Conductivity 46
2.2.2 Classes of Conducting Materials 47
2.2.3 Energy Bands and Origin of Transport
Properties 47
2.2.4 Thermal Dependence of Conductivity 49
2.2.5 Types of Semiconducting Materials:
Chemical and Electrochemical Doping 51
2.2.6 Band Theory of Solids: A Closer Look
at the Band Structure 53
2.2.7 Structural Anisotropy and Peierls
Distortion 58
2.3 Principles of Molecular Photophysics 60
2.3.1 Electromagnetic Radiation and
Light–Matter Interaction 61
2.3.2 Electronic Energy States 63
2.3.2.1 Electronic, rotational, and
vibrational states 63
2.3.2.2 Absorption of radiation 65
2.3.2.3 Transition moment integral
and selection rules 68
2.3.2.4 The Franck–Condon principle 75
2.3.3 Evolution of Excited States 78
2.3.3.1 Luminescence 78
2.3.3.2 Kasha’s rule 81
2.3.3.3 Fluorescence and
phosphorescence 83
2.3.3.4 Luminescent and
nonluminescent molecules 85
2.3.3.5 Jablonski diagram 86
2.3.4 Emission Efficiency 88
2.3.4.1 Quantum yield and
luminescence quenching 88
2.3.4.2 Kinetics of photophysical
processes 90
2.3.4.3 Emission lifetime 92
 Contents vii

2.3.4.4 Dynamics of radiative decay 94

2.3.5 Energy Transfer 96
2.3.5.1 Dexter’s energy transfer 98
2.3.5.2 Förster’s energy transfer 99
2.3.6 Quenching 102
2.3.6.1 Dynamic and static quenching 102
2.3.7 Metal-Centered Electronic Transitions 107
2.3.7.1 d–d transitions 109
2.3.7.2 f-f transitions 112
2.3.8 Nonlinear Molecular Optics 119

3. Functional Molecular Materials 127

3.1 Magnetic Molecular Materials 127
3.1.1 Paramagnetism 128
3.1.2 Ferromagnetism 133
3.1.3 Antiferromagnetism 145
3.1.4 Ferrimagnetism 149
3.1.5 Spin Crossover 155
3.1.6 Valence Tautomerism 167
3.1.7 Slow Magnetic Relaxation 175
3.1.7.1 Single-molecule magnets 176
3.1.7.2 Single-ion magnets 190
3.1.7.3 Single-chain magnets 193
3.1.7.4 Molecular spin qubits 197
3.2 Conducting Molecular Materials 208
3.2.1 Charge Transfer Salts 210
3.2.2 Radical Cation Salts 212
3.2.3 Radical Anion Salts 219
3.2.4 Single-Component Molecular
Conductors 221
3.2.5 Chiral Molecular Conductors 222
3.2.5.1 Enhanced conductivity in
enantiopure chiral conductors 222
3.2.5.2 Electrical magnetochiral
anisotropy 223
3.2.6 General Considerations 224
3.3 Optical Molecular Materials 225
3.3.1 Electronic Transitions and Light
Absorption in Metal Complexes 227
viii Contents

3.3.1.1 Structural/optical properties

relationship 229
3.3.1.2 Energy 230
3.3.1.3 Intensity 232
3.3.2 Luminophores with a Structural Role
of the Metal 233
3.3.2.1 Effect of the metal 236
3.3.2.2 Effect of the ligand 238
3.3.2.3 Supramolecular effects 239
3.3.3 Luminophores Based on Open-Shell
d-Metal Complexes 242
3.3.3.1 First-row transition metal
complexes 244
3.3.3.2 Second- and third-row
transition metal complexes 246
3.3.4 Luminophores Based on Lanthanide
Complexes 259
3.3.4.1 Ligand-to-metal sensitization 264
3.3.4.2 Sensitized lanthanide emission 273
3.3.4.3 Advanced molecular design
and general considerations 284
3.3.5 Molecular NLOphores 288
3.3.5.1 SHG NLOphores 288
3.3.5.2 General considerations 299

4. Multifunctional Molecular Materials 301

4.1 A Family of Paramagnetic Superconductors 302
4.2 Magnetic-Field-Induced Superconductivity
in a Paramagnetic Metal 306
4.3 Ferromagnetic Metal-Like Conductors 308
4.4 Coexistence of Electrical Conductivity and
Slow Magnetic Relaxation in a Hybrid Material 313
4.5 Synergism between Electrical Conductivity
and Spin-Crossover Behavior 317
4.6 A Molecular Ferromagnet with an Increased
Coercive Field 321
4.7 Optical Control in a Chiral Photomagnet 325
4.8 Multiemissive Molecular Materials 329
4.8.1 Superimposed Optical Properties 331
4.8.2 Cooperative Optical Properties 334
 Contents ix

4.9 Conducting Luminescent Materials 337

5. Turning Molecular Materials into Devices 341

5.1 Organic Light-Emitting Diodes 342
5.2 Optical Fibers and Amplifiers for
Telecommunication 347
5.3 Dye-Sensitized Solar Cells 353
5.4 Single-Molecule Magnets on the Surface 362
5.5 Light-Induced Spin-Crossover Dynamics on
the Surface 366

Bibliography 371

Index 385
 Preface

The field of molecular materials represents an exciting playground

for the design, tailoring, and combination of chemical building blocks
as carriers of physical properties and aims at the understanding and
development of novel functional molecular devices. Thanks to the
countless possibilities to associate diverse chemical assemblies and
physical properties, infinite different materials can be, in principle,
foreseen.
Within this extraordinarily widespread framework, the
realization of materials with the desired functionalities can
only be achieved through a rational design strategy based on a
solid understanding of the chemical/physical features of each
constituting building block. This required background knowledge
can be acquired thanks to an extensive existing literature providing
exhaustive reviews on important topics and classes of molecular
materials, owing to the contributions of authors who are recognized
authorities in quite specific fields. While these volumes are, indeed,
of great value to expert scientists, as the contents are addressed
at a high and rigorous scientific level, they might be nonetheless
challenging reading for early-stage researchers entering this field.
The basic idea behind this book is therefore to provide a general
overview of molecular materials, discussing their key features
in a simple and organic way and focusing more on basic concepts
rather than on specialized descriptions, in order to supply the
nonexpert reader with the immediate fundamental tools and hints
to understand and develop research in this field.
With this view, this textbook is intended as a step-by-step guide
toward the preparation of functional molecular materials, where
the knowledge and understanding so far attained by the scientific
community through the investigation of significant archetypical
examples are deconstructed down to the fundamentals and then
presented from the bottom to the top.
After a brief introduction to the key features of molecular
materials (Chapter 1), basic concepts of molecular magnetism,
conductivity, and molecular photophysics are discussed (Chapter
xii Preface

2). Different classes of functional molecular materials are presented

by taking advantage of selected relevant compounds reported
in the literature (Chapter 3). The reader will be then guided to
design multifunctional molecular materials with predesigned
functionalities, taking into account the chemical/structural features
and the physical properties of specific molecular building blocks
(Chapter 4). Finally, selected applications of molecular materials
for device preparation and challenging experiments in the field are
discussed (Chapter 5).
The original purpose behind material design is analyzed and the
physical properties explained on a fundamental basis throughout the
book. In addition, the correlation between structure and properties
is thoroughly discussed with the aim to provide evidence of the
importance of considering the interplay between these aspects in
obtaining a desired material. Relevant and recent examples have
been selected so that experts in this field also may retrieve useful
information.
Functional Molecular Materials: An Introductory Textbook is
intended as a general, easy-to-read, and practical reference textbook
the authors themselves would have liked to read in the early stages
of their research career, and it has been written in the hope of
providing a useful starting guide for future scientists in the field.
Matteo Atzori
Flavia Artizzu
2018
Chapter 1

Introduction to Molecular Materials

The aim of this chapter is to introduce the reader to the concept of

molecular materials by defining what they are and what distinguishes
them from the more conventional atom-based systems. The general
ideas that drive the approach to the design and preparation of
molecular materials will be presented, shedding light on the
enormous potentialities that this field can offer in the development
of new technologically advanced applications.

1.1 What Are Molecular Materials?

A molecular material can be defined as a material built by molecules
responsible for specific functionalities that can be potentially used
for a certain technological application. Given the large number of
diverse physical properties that a molecule can feature and the wide
range of research fields to which they belong, it appears clear that
the number of classes and types of systems that can be categorized
under the term “molecular materials” is enormous. One classification
can be related to the nature of the physical properties shown by such
systems, more specifically, associating them to the areas of solid-
state physics, that is, magnetism, optics, and electronics. Therefore,
we can talk about molecular materials that show magnetic, optical,
or electrical properties, independently of the nature and complexity
of the molecules that originate them (Fig. 1.1).

Functional Molecular Materials: An Introductory Textbook

Matteo Atzori and Flavia Artizzu
Copyright © 2018 Pan Stanford Publishing Pte. Ltd.
ISBN 978-981-4774-76-5 (Hardcover), 978-1-351-23366-8 (eBook)
www.panstanford.com
2 Introduction to Molecular Materials

Figure 1.1 Some examples of molecular materials with relevant technological

applications categorized as a function of their physical properties.

As far as the nature of these materials is concerned, we can

define as molecular materials all those systems based on molecular
units, both organic and inorganic, or a combination of them (hybrid
systems), whose physical properties arise from the peculiar nature of
the single molecular entity or from particular interactions occurring
between molecules with specific structural and electronic features.
The first case is referred to as a single-molecule property, that
is, one molecule able to show the same physical behavior as that
observed for the bulk material at the molecular scale, whereas the
second case is related to a cooperative property that arises from
key interactions between a number of molecules that, if isolated,
do not show any relevant physical property or, in some cases, a
different one. From these considerations it may appear evident
that molecular materials mostly belong to the fields of molecular
inorganic/coordination chemistry, supramolecular chemistry, and
 What Are Molecular Materials? 3

organic chemistry. A variety of molecular architectures, such as

transition metals or lanthanide-based complexes (mononuclear
or multinuclear, homometallic or heterometallic, homoleptic or
heteroleptic), coordination or supramolecular polymers with
various dimensionalities (1D, 2D, or 3D), and redox-active and/or
p-delocalized organic molecules, can be counted among this class.
One of the most intriguing potentialities of molecular materials
lies in the extraordinary versatility of their chemistry, which
allows, in principle, the tailoring of their physical behavior and
the opportunity to afford systems showing multiple functionalities
at the molecular or supramolecular level. Systems exhibiting a
single physical property are commonly called monofunctional
molecular materials, while those exhibiting any combination of
the aforementioned functionalities are multifunctional molecular
materials. Although the coexistence of multiple physical properties
in a single molecular system is not uncommon, generally, the most
pursued strategy to achieve multifunctional molecular materials
consists of the proper combination of selected monofunctional
molecular materials exploiting the principles of molecular self-
assembly.1 Monofunctional molecular materials showing the
additional feature of being suitable to be combined with each other
can be called building blocks, after their usage as molecular bricks
for the construction of more sophisticated architectures, whether
molecular, supramolecular, or nanostructured, which multifunctional
molecular materials are based on (Fig. 1.2).

Figure 1.2 Schematic representation of two types of generic molecular

building blocks (left and right) that self-assemble in a more sophisticated
architecture (middle).
1Molecular self-assembly defines a process in which preformed molecular building

blocks initially disposed in a random configuration interact with each other through
specific interactions, not dictated by external factors, leading to an organized
molecular or supramolecular structure.
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