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Chemical Wiring and Soldering toward All- Molecule Electronic Circuitry Tobe Lab. Daichi Ando Masakazu Aono et al., J. Am. Chem. Soc., 2011, 133 (21), 8227

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Page 1: Chemical Wiring and Soldering toward All-Molecule Electronic Circuitry Tobe Lab. Daichi Ando Masakazu Aono et al., J. Am. Chem. Soc., 2011, 133 (21), 8227

Chemical Wiring and Soldering toward All-Molecule Electronic

Circuitry

Tobe Lab.Daichi Ando

Masakazu Aono et al., J. Am. Chem. Soc., 2011, 133 (21), 8227

Page 2: Chemical Wiring and Soldering toward All-Molecule Electronic Circuitry Tobe Lab. Daichi Ando Masakazu Aono et al., J. Am. Chem. Soc., 2011, 133 (21), 8227

Contents

Introduction Single-molecule electronics Linear chain polymerization Purpose of this work

Result and discussion Adsorption of CuPc Chemical Sodering

Conclusion

Page 3: Chemical Wiring and Soldering toward All-Molecule Electronic Circuitry Tobe Lab. Daichi Ando Masakazu Aono et al., J. Am. Chem. Soc., 2011, 133 (21), 8227

Single-Molecule Electronics

Díez-Perez, I.; Tao, N. Nat. Chem. 2009, 1, 635–641.

Barner, J.; Rabe, J. P. Macromol. Rapid Commun. 2010, 31, 362–367.

Rectification = 整流性

Page 4: Chemical Wiring and Soldering toward All-Molecule Electronic Circuitry Tobe Lab. Daichi Ando Masakazu Aono et al., J. Am. Chem. Soc., 2011, 133 (21), 8227

Linear chain polymerization

RC

CC

CR

CC

CC

R

RC

CC

C

R

R

RC

CC

CR

RC

CC

CR

RC

CC

CR R C

CC

C RR C

CC

C R

R CC

CC R

UV photons addition

Monmer Radical Polymer

Okawa, Y.; Aono, M. J. Chem. Phys. 2001, 115, 2317–2322.

Page 5: Chemical Wiring and Soldering toward All-Molecule Electronic Circuitry Tobe Lab. Daichi Ando Masakazu Aono et al., J. Am. Chem. Soc., 2011, 133 (21), 8227

Purpose of This Work

Monomer molecules of the diacetylene form a self-assembled monolayer (SAM).

Stimulation from the STM tip initiates the chain polymerization of the diacetylene (PDA).

The lifted-up structure of PDA enables the reactive end to approach the adsorbed molecule.

Page 6: Chemical Wiring and Soldering toward All-Molecule Electronic Circuitry Tobe Lab. Daichi Ando Masakazu Aono et al., J. Am. Chem. Soc., 2011, 133 (21), 8227

Adsorption of CuPc

N N

NNCu

Cupper Phthalocyanine (CuPc)

O

OH

10, 12-nonacosadiynoic acid (diacetylene molecule)

Page 7: Chemical Wiring and Soldering toward All-Molecule Electronic Circuitry Tobe Lab. Daichi Ando Masakazu Aono et al., J. Am. Chem. Soc., 2011, 133 (21), 8227

Chmical Soldering

About 70% of the STM images showed type A.

Page 8: Chemical Wiring and Soldering toward All-Molecule Electronic Circuitry Tobe Lab. Daichi Ando Masakazu Aono et al., J. Am. Chem. Soc., 2011, 133 (21), 8227

The Density-functional First-Principles Method

Page 9: Chemical Wiring and Soldering toward All-Molecule Electronic Circuitry Tobe Lab. Daichi Ando Masakazu Aono et al., J. Am. Chem. Soc., 2011, 133 (21), 8227

The Calculated Distribution

NN

NN

Cu

R

R

RC

R

RR

R

R

R

sp sp sp sp sp

sp2 sp2 sp2 sp2

sp3

Page 10: Chemical Wiring and Soldering toward All-Molecule Electronic Circuitry Tobe Lab. Daichi Ando Masakazu Aono et al., J. Am. Chem. Soc., 2011, 133 (21), 8227

Polarons and Bipolarons

Acceptor

unpaired electron

positive charge

polaron

bipolaron

Page 11: Chemical Wiring and Soldering toward All-Molecule Electronic Circuitry Tobe Lab. Daichi Ando Masakazu Aono et al., J. Am. Chem. Soc., 2011, 133 (21), 8227

PDA-ZnPc-PDA System

Page 12: Chemical Wiring and Soldering toward All-Molecule Electronic Circuitry Tobe Lab. Daichi Ando Masakazu Aono et al., J. Am. Chem. Soc., 2011, 133 (21), 8227

Contents

Page 13: Chemical Wiring and Soldering toward All-Molecule Electronic Circuitry Tobe Lab. Daichi Ando Masakazu Aono et al., J. Am. Chem. Soc., 2011, 133 (21), 8227

Conclusion

・ Conductive polymer nanowires connect to   a functional molecule via covalent bonds.

・ This method represents a key step in advancing the development of future single-molecule circuits.

・ Polymer connection to phthalocyanine (chemical soldering) is the main reaction.