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Short Literature 11/15/10 Dustin Raup

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Page 1: Short Literature - cpb-us-e1.wpmucdn.com · 11/11/2011  · 60 °C 20 °C 280 nm 280 nm 380 nm 380 nm Nature, 1999, 401, 152-155 First Report of Continuous Unimolecular Motion by

Short Literature11/15/10

Dustin Raup

Page 2: Short Literature - cpb-us-e1.wpmucdn.com · 11/11/2011  · 60 °C 20 °C 280 nm 280 nm 380 nm 380 nm Nature, 1999, 401, 152-155 First Report of Continuous Unimolecular Motion by

Prof. Ben Feringa

- PhD in 1978 with Prof. Hans Wynberg (Univ. of Groningen)- Research Scientist with Royal Dutch Shell (1978-1984)- Lecturer in Organic Chemistry, Univ. of Groningen (1984-1988)- Prof. of Organic Chemistry (1988-present)- Department Chair (1991-1995)- Director Stratingh Institute for Chemistry (2003-present)- J. H. vanʼt Hoff Distinguished Prof. (2003-present)- Academy Professor, Royal Netherlands Acad. of Sciences- Editor of Organic & Biomolecular Chemistry

Research Focus:

Asymmetric CatalysisChirality

Biomimetic and Catalytic OxidationOrganogels and Smart MaterialsMolecular Switches and Motors

Page 3: Short Literature - cpb-us-e1.wpmucdn.com · 11/11/2011  · 60 °C 20 °C 280 nm 280 nm 380 nm 380 nm Nature, 1999, 401, 152-155 First Report of Continuous Unimolecular Motion by

Molecular Motors

Inspiration from Nature

Bacterial flagellum translate molecular motion to do locomotive work!

Page 4: Short Literature - cpb-us-e1.wpmucdn.com · 11/11/2011  · 60 °C 20 °C 280 nm 280 nm 380 nm 380 nm Nature, 1999, 401, 152-155 First Report of Continuous Unimolecular Motion by

Molecular Motor Applications

Controlling the properties of liquid crystal films

S

S

S

S

hvMe

Me

Me

Me

Molecular “brakes” or Switches

Fast Propellers for microfluidics

Page 5: Short Literature - cpb-us-e1.wpmucdn.com · 11/11/2011  · 60 °C 20 °C 280 nm 280 nm 380 nm 380 nm Nature, 1999, 401, 152-155 First Report of Continuous Unimolecular Motion by
Page 6: Short Literature - cpb-us-e1.wpmucdn.com · 11/11/2011  · 60 °C 20 °C 280 nm 280 nm 380 nm 380 nm Nature, 1999, 401, 152-155 First Report of Continuous Unimolecular Motion by

Unidirectional Light-Driven Molecular Motors

Me Me

Me Me

Me

Me

Me

Me

20 °C60 °C

280 nm

280 nm

380 nm

380 nm

Nature, 1999, 401, 152-155

First Report of Continuous Unimolecular Motion by Feringa

Page 7: Short Literature - cpb-us-e1.wpmucdn.com · 11/11/2011  · 60 °C 20 °C 280 nm 280 nm 380 nm 380 nm Nature, 1999, 401, 152-155 First Report of Continuous Unimolecular Motion by

Synthesis of the New System

SH 1. NEt3, toluene, 50 °C

OO O

2. AlCl3, 0 - 22 °C

67% over 2 steps

S

O

OH

O 1. EDC, HOBT, NHNMe2, DIPEACH2Cl2, rt, 83%

2. NHNH2, EtOH55%

S

N

NMe2

O

NH2

I OAcOAc

S

N

NMe2

O

N

S

S

DMF -50 to 22 °C55%

SNMe2

O

S

S

SNMe2

O

S

PPh3, 80 °C

92%

Barton-Kellogg Diazo-thioketone coupling

Page 8: Short Literature - cpb-us-e1.wpmucdn.com · 11/11/2011  · 60 °C 20 °C 280 nm 280 nm 380 nm 380 nm Nature, 1999, 401, 152-155 First Report of Continuous Unimolecular Motion by

Schematic of How the Bidirectional System Works

Page 9: Short Literature - cpb-us-e1.wpmucdn.com · 11/11/2011  · 60 °C 20 °C 280 nm 280 nm 380 nm 380 nm Nature, 1999, 401, 152-155 First Report of Continuous Unimolecular Motion by

How The New System Works

S

S

O

NMe

Me S

S

O

NMe

MeS

S

O

NMe

Me S

S

O

NMe

Me

S

S

O

NMe

Me S

S

O

NMe

MeS

S

O

NMe

Me S

S

O

NMe

Me

hv hv

hvhv

base

base

heatheatheatheat

Page 10: Short Literature - cpb-us-e1.wpmucdn.com · 11/11/2011  · 60 °C 20 °C 280 nm 280 nm 380 nm 380 nm Nature, 1999, 401, 152-155 First Report of Continuous Unimolecular Motion by
Page 11: Short Literature - cpb-us-e1.wpmucdn.com · 11/11/2011  · 60 °C 20 °C 280 nm 280 nm 380 nm 380 nm Nature, 1999, 401, 152-155 First Report of Continuous Unimolecular Motion by

The Pauson-Khand Reaction

- Cobalt alkyne complex first reported in 1971, by Pauson and Khand, reaction run but uncharacterized.- Complex first intercepted and characterized by Nicholas in the Nicholas Reaction- Formal [2+2+1] cycloaddition of alkyne, alkene and CO reported by Pauson and Khand in 1973.

R1 R2

R3

COCo2(CO)6 R1

R1

R1

O

R1OH

Co2(CO)6

then oxidantR1

Nuc

R2

R2NucH

Pauson-Khand

Nicholas

Page 12: Short Literature - cpb-us-e1.wpmucdn.com · 11/11/2011  · 60 °C 20 °C 280 nm 280 nm 380 nm 380 nm Nature, 1999, 401, 152-155 First Report of Continuous Unimolecular Motion by

Mechanism

(CO)3Co Co(CO)3

R1 R2

(CO)3Co Co(CO)3R1 R2 Co(CO)3

Co(CO)3

R1

R2

-COCo(CO)3Co(CO)2

R1

R2

R3Co(CO)3Co(CO)2

R1

R2

R3

Co(CO)3Co(CO)3

R1

R2

+CO

+CO

R3

Co(CO)3Co(CO)3

R1

R2

OR3OR3

R2

R1Co(CO)3Co(CO)3

OR3

R2

R1

Page 13: Short Literature - cpb-us-e1.wpmucdn.com · 11/11/2011  · 60 °C 20 °C 280 nm 280 nm 380 nm 380 nm Nature, 1999, 401, 152-155 First Report of Continuous Unimolecular Motion by

Visible Light Activated Pauson-Khand

HH R

H

O

R

XS

1 atm COCo2(CO)6

22 °C

halogen lampor sunlight

HH

O

ferrocene

HH

O

TMS

78% 78%

Page 14: Short Literature - cpb-us-e1.wpmucdn.com · 11/11/2011  · 60 °C 20 °C 280 nm 280 nm 380 nm 380 nm Nature, 1999, 401, 152-155 First Report of Continuous Unimolecular Motion by

Using Light for Activation?

Prior Art

HH R

H

O

R

XS

1 atm COCo2(CO)6

22 °C

halogen lampor sunlight

HH R

H

O

R

XS

1 atm COCo2(CO)6

22 °C

halogen lampor sunlight

- Alkyne-Co complex undergoes homolytic bond cleavage in light and radicals

- Suggests that light facilitates loss of CO ligand (RDS as as suggested by Magnus and coworkers)

TEMPO22 °C

300 nm hvheat

37-99% yield

Org. Lett., 2005, 7 (14), pp 3033–3036

up to 95% yield


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