Synthesis of Conjugated Polymers from Surface Confined Highly Reactive Butadiyne Derivatives Tobe labratory Daichi Ando

Introduction Topochemical Polymerization 10,12-Nonacosadiynoic acid Phthalocyanine STM Tip Okawa, Y.; Aono, M. J. Am. Chem. Soc. xxxx, xxx,

Contents ・ STM ( Scanning Tunneling Microscope ) ・ Self-Assembly ・ Radical Polymerization ・ Background and Purpose of my project

STM Observations of Nanostructure Graphite Surface Au(111) Surface 1nm Ore of Gold （金の原石） Graphite STM PicoSTM (Agilent) Nanoscope IIIa (Digital lab.

5 Scanning Tunneling Microscopy (STM) e - V I d d I Quantum Tunneling d STM schematic diagram I = Ve -cd Tip Surface: Ag(111)

What’s Self - Assembly ? Water Droplets on Cold Glass Surface Product of Alum( ミョウバン ) DisorderOrder

Hydrogen bonding Self-Assembly van der Waals interaction 2D nano-architectures are constructed by molecular self-assembly. Heckl, W. M. et al. Single Mol. 2002, 3, 25.Charra, F. et al. Nano Lett. 2006, 6, 1360.

Hydrogen bond 8 Intermolecular interaction -Hydrogen bond- Lackinger, M.; Griessl, S.; Heckl, W. M.; Hietschold, M.; Flynn, G. W.; Langmuir, 2005, 21, Honeycomb( 蜂の巣 )

Intermolecular interaction -Van der Waals interaction- Van der waals interaction Bléger, D.; Kreher, D.; Mathevet, F.; Attias, A.-J.; Schull, G.; Huard, A.; Douillard, L.; Fiorini-Debuischert, C.; Charra, F. Angew. Chem. Int. Ed. 2007, 46, 7404–

Homlytic Cleavage ( ホモリシス開裂 ) Radical Polymerization ( ラジカル重合 ) Radical Radical Polymerization Radical Stylene

Topochemical Polymerization of Butadiyne Derivatives on Surface Okawa, Y.; Aono, M. J. Chem. Phys. 2001, 115, Monomer molecule Chain propagation

Previous Research Octaehydrobenzo[12]annulene Derivatives Polymerization Octadehydrobenzo[12]annulene (DBA) Tobe, Y. et al. Chem. Eur. J. 2010, 16, – 6.1 nm

Purpose of This work external stimuliPolymerization Polyacene Radical Intermediate Previous SubjectFollowing Subject

SnowflakeFeather of Peafowl Zebra’s pattern Heartbeat What’s Self - Assembly ?

Topochemical Polymerization of Butadiyne Derivatives on Surface Okawa, Y.; Aono, M. J. Chem. Phys. 2001, 115, Monomer molecule h Electronic excitation Vibration excitation Addition reaction Chain propagation

Dehydrobenzo[12]annulene Derivatives Zhou, Q.; Carrol, P. J.; Swager, T. M. J. Org. Chem. 1994, 59, a: R = C 10 H 21 1b: R = OC 12 H 25 1c: R = OC 14 H 29 1d: R = OC 16 H 33 1e: R = OC 18 H 37 1f: R = OC 20 H 41 Polymerization Octadehydrobenzo[12]annulene (DBA) 1 1a Tobe, Y. et al. Chem. Eur. J. 2010, 16, – 6.1 nm

h or pulse voltage