Fragments of Fullerenes and Carbon Nanotubes Designed Synthesis, Unusual Reactions, and Coordination Chemistry

This book is the first of its kind to reflect upon the intense and rapidly growing interest in open geodesic polyaromatic molecules, specifically focusing on their synthesis and reactivity in metal binding reactions.   The book broadly covers all aspects related to the fullerene fragment chemistry: current synthetic techniques, description of the available members of this new family (which has grown to more than two dozens members, with none being available commercially), molecular geometry and trends in the solid state packing, as well as extensions into physical properties and new buckybowl-based molecules and materials.  It covers fundamental research related to a new class of hydrocarbons, namely open geodesic polyarenes that map onto the surfaces of fullerenes (and referred to as fullerene fragments or buckybowls.

Marina A. Petrukhina received her PhD from Moscow State University in 1988 and is a Professor in the Department of Chemistry at the University of Albany. She has published over 120 research papers in scientific journals. In 2006, she received the NSF Career Award, a five-year grant to explore the reactivity and coordination limits of open geodesic polyaromatic hydrocarbons (buckybowls).

Lawrence T. Scott received his PhD from Harvard University in 1970 and is a Professor at Boston College, where he occupies the Louise and Jim Vanderslice and Family Chair in Chemistry. He has published more than 200 research papers in scientific journals and currently serves on the editorial advisory boards for Polycyclic Aromatic Compounds and The Journal of Organic Chemistry.  In 2011, he received the George A. Olah Award in Hydrocarbon Chemistry from the American Chemical Society.

PREFACE vii

FOREWORD xi

CONTRIBUTORS xiii

ACRONYMS xvii

1 MOLECULAR CLIPS AND TWEEZERS WITH CORANNULENE PINCERS 1
Andrzej Sygula and Willard E. Collier

2 SYNTHESIS OF BOWL-SHAPED AND BASKET-SHAPED FULLERENE FRAGMENTS VIA BENZANNULATED ENYNE---ALLENES 41
Kung K. Wang, Hu Cui, and Bo Wen

3 ANIONS OF BUCKYBOWLS 63
David Eisenberg, Roy Shenhar, and Mordecai Rabinovitz

4 CURVED p-CONJUGATED STABLE OPEN-SHELL SYSTEMS POSSESSING THREE-DIMENSIONAL MOLECULAR/ELECTRONIC SPIN STRUCTURES 95
Yasushi Morita and Akira Ueda

5 EXPERIMENTAL AND CALCULATED PROPERTIES OF FULLERENE AND NANOTUBE FRAGMENTS 135
Derek R. Jones, Praveen Bachawala, and James Mack

6 COORDINATION PREFERENCES OF BOWL-SHAPED POLYAROMATIC HYDROCARBONS 157
Alexander S. Filatov and Marina A. Petrukhina

7 SUMANENES: SYNTHESIS AND COMPLEXATION 187
Toshikazu Hirao and Toru Amaya

8 r-BONDED TRANSITION METAL COMPLEXES OF POLYCYCLIC AROMATIC CARBON COMPOUNDS 205
Paul R. Sharp

9 HEMISPHERICAL GEODESIC POLYARENES: ATTRACTIVE TEMPLATES FOR THE CHEMICAL SYNTHESIS OF UNIFORM-DIAMETER ARMCHAIR NANOTUBES 235
Anthony P. Belanger, Katharine A. Mirica, James Mack, and Lawrence T. Scott

10 AROMATIC BELTS AS SECTIONS OF NANOTUBES 259
Gaston R. Schaller and Rainer Herges

11 CYCLOPARAPHENYLENES: THE SHORTEST POSSIBLE SEGMENTS OF ARMCHAIR CARBON NANOTUBES 291
Xia Tian and Ramesh Jasti

12 CONJUGATED MOLECULAR BELTS BASED ON 3D BENZANNULENE SYSTEMS 311
Masahiko Iyoda, Yoshiyuki Kuwatani, Tohru Nishinaga, Masayoshi Takase, and Tomohiko Nishiuchi

13 TOWARD FULLY UNSATURATED DOUBLE-STRANDED CYCLES 343
Malte Standera and A. Dieter Schl€uter

14 BENT PYRENES: SPRINGBOARDS TO AROMATIC BELTS? 367
Graham J. Bodwell, Gandikota Venkataramana, and Unikela Kiran Sagar

INDEX 401