pi-logic Veen, Maria Helena van der
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1 pi-logic Veen, Maria Helena van der IMPORTANT NOTE: You are advised to consult the publisher's version (publisher's PDF) if you wish to cite from it. Please check the document version below. Document Version Publisher's PDF, also known as Version of record Publication date: 2006 Link to publication in University of Groningen/UMCG research database Citation for published version (APA): Veen, M. H. V. D. (2006). pi-logic [Groningen]: s.n. Copyright Other than for strictly personal use, it is not permitted to download or to forward/distribute the text or part of it without the consent of the author(s) and/or copyright holder(s), unless the work is under an open content license (like Creative Commons). Take-down policy If you believe that this document breaches copyright please contact us providing details, and we will remove access to the work immediately and investigate your claim. Downloaded from the University of Groningen/UMCG research database (Pure): For technical reasons the number of authors shown on this cover page is limited to 10 maximum. Download date:
2 π-logic
3 Cover Based on Escher-type artwork provided by Dr. Joseph L. Teeters π-logic M.H. van der Veen Ph.D. Thesis University of Groningen, The Netherlands May 2006 The work described in this thesis was performed in the research group Chemistry of (Bio)Molecular Materials and Devices of the Stratingh Instituut, University of Groningen, The Netherlands. The work described in this thesis was financially supported by the MSC plus. MSC plus Ph.D. thesis series ISSN ISBN (paperback version) ISBN (electronic version) Publisher Rijksuniversiteit Groningen, Groningen, The Netherlands Printing Grafisch bedrijf Ponsen & Looijen BV, Amsterdam, The Netherlands Copyright 2006, M. H. van der Veen All rights reserved. No part of this publication may be reproduced, stored in a retrieval system, or transmitted, in any form or by any means, electronic, mechanical, photocopying, recording, or otherwise, without permission from the author.
4 RIJKSUNIVERSITEIT GRONINGEN π-logic Proefschrift ter verkrijging van het doctoraat in de Wiskunde en Natuurwetenschappen aan de Rijksuniversiteit Groningen op gezag van de Rector Magnificus, dr. F. Zwarts, in het openbaar te verdedigen op maandag 22 mei 2006 om uur door Maria Helena van der Veen geboren op 13 januari 1978 te Hoogeveen
5 Promotor: Copromotor: Prof. dr. J. C. Hummelen Dr. H. T. Jonkman Beoordelingscommissie: Prof. dr. J. Knoester Dr. S. Roth Prof. dr. F. Wudl
6 Voor wie het leest Yesterday is history Today is a gift Tomorrow is mystery Mysteryland, 2005
7
8 Contents 1 Molecular Electronics On the Way to Molecular Electronics The Conjugated Double Bond Topological Aspects of Quasi-particles Valence Bond Theory and Molecular Orbital Theory Molecular Scale Electronics Challenges Thesis objectives References 21 2 On the Classification of n-terminal π-conjugated Systems Introduction Systematic Analysis of n-terminal Systems Analysis of Fully Unsaturated n-terminal Systems: Fundamentals, Definitions, and Conventions Classification of n-terminal π-conjugated Systems Generalized Analysis of n-terminal Systems Discussion Conclusions References and Notes 49 3 Topological Design of Omniconjugated Systems Introduction Wiring Molecular Wires Design of Omniconjugated Models Topological Design Program Type B Omniconjugated Models Quasi-omniconjugated Models Topological Properties of Omniconjugated Models Classification of n-terminal π-conjugated Systems: Extended Real Chemical Examples of Omniconjugated Compounds Conclusions References and Notes 82
9 π-logic 4 Electronic structure of Omniconjugated compounds Introduction Quantum-Chemical approach Frontier Orbital Delocalization Frontier Orbital Localization Discussion and Conclusions References 98 5 Group Theoretical Aspects: A Quest for Control and Understanding Introduction The Symmetry Properties of n-terminal Systems The Construction of a Group based on π-topology The Basis for Understanding π-topological Properties Mathematical Basis for the Design of π-logic Discussion Conclusions References and Notes π-logic: Topologies for Boolean Functions inside Single π-conjugated Molecules Introduction Logic Gates from Two Switches Based on π-conjugation All Boolean Functions inside Compact π-logic Gates Increasing the Complexity: Bifunctional Logic Elements On the Built-in Logic of n-terminal π-conjugated Systems Discussion and Conclusions References and Notes 151 Appendix A 5-Terminal Archetype Series 155 Appendix B G 5A Group Multiplication Table 156 Appendix C 6-Terminal Archetype Series 157 Appendix D Truth Tables of Boolean Functions 158 2
10 Contents Summary 159 Samenvatting 161 Dankwoord 167 3
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