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Page 1: R1 R2 E1 E2 H H 0.35 0.77 Me Me 0.26 0.62 OMe OMe 0.44 0.68 SMe SMe 0.51 0.78 (CH=CH)2 (CH=CH)2 0.62 0.94 SMe H 0.44 0.77 SMe CO2Me 0.83 1.22 SMe CN 1.04 1.32 V vs. SCE, in PhCN, Bu4NClO4

HOMO LUMO

Page 2: R1 R2 E1 E2 H H 0.35 0.77 Me Me 0.26 0.62 OMe OMe 0.44 0.68 SMe SMe 0.51 0.78 (CH=CH)2 (CH=CH)2 0.62 0.94 SMe H 0.44 0.77 SMe CO2Me 0.83 1.22 SMe CN 1.04 1.32 V vs. SCE, in PhCN, Bu4NClO4

25°C

Page 3: R1 R2 E1 E2 H H 0.35 0.77 Me Me 0.26 0.62 OMe OMe 0.44 0.68 SMe SMe 0.51 0.78 (CH=CH)2 (CH=CH)2 0.62 0.94 SMe H 0.44 0.77 SMe CO2Me 0.83 1.22 SMe CN 1.04 1.32 V vs. SCE, in PhCN, Bu4NClO4
Page 4: R1 R2 E1 E2 H H 0.35 0.77 Me Me 0.26 0.62 OMe OMe 0.44 0.68 SMe SMe 0.51 0.78 (CH=CH)2 (CH=CH)2 0.62 0.94 SMe H 0.44 0.77 SMe CO2Me 0.83 1.22 SMe CN 1.04 1.32 V vs. SCE, in PhCN, Bu4NClO4
Page 5: R1 R2 E1 E2 H H 0.35 0.77 Me Me 0.26 0.62 OMe OMe 0.44 0.68 SMe SMe 0.51 0.78 (CH=CH)2 (CH=CH)2 0.62 0.94 SMe H 0.44 0.77 SMe CO2Me 0.83 1.22 SMe CN 1.04 1.32 V vs. SCE, in PhCN, Bu4NClO4

NHE: 2H+ + 2e = H2

Page 6: R1 R2 E1 E2 H H 0.35 0.77 Me Me 0.26 0.62 OMe OMe 0.44 0.68 SMe SMe 0.51 0.78 (CH=CH)2 (CH=CH)2 0.62 0.94 SMe H 0.44 0.77 SMe CO2Me 0.83 1.22 SMe CN 1.04 1.32 V vs. SCE, in PhCN, Bu4NClO4

-

i = nFv

Ox + ne- Red

Page 7: R1 R2 E1 E2 H H 0.35 0.77 Me Me 0.26 0.62 OMe OMe 0.44 0.68 SMe SMe 0.51 0.78 (CH=CH)2 (CH=CH)2 0.62 0.94 SMe H 0.44 0.77 SMe CO2Me 0.83 1.22 SMe CN 1.04 1.32 V vs. SCE, in PhCN, Bu4NClO4

Ox

Page 8: R1 R2 E1 E2 H H 0.35 0.77 Me Me 0.26 0.62 OMe OMe 0.44 0.68 SMe SMe 0.51 0.78 (CH=CH)2 (CH=CH)2 0.62 0.94 SMe H 0.44 0.77 SMe CO2Me 0.83 1.22 SMe CN 1.04 1.32 V vs. SCE, in PhCN, Bu4NClO4

Red Ox + ne-

(a) Red

(b) ( )

Ox

(b)

( )

Page 9: R1 R2 E1 E2 H H 0.35 0.77 Me Me 0.26 0.62 OMe OMe 0.44 0.68 SMe SMe 0.51 0.78 (CH=CH)2 (CH=CH)2 0.62 0.94 SMe H 0.44 0.77 SMe CO2Me 0.83 1.22 SMe CN 1.04 1.32 V vs. SCE, in PhCN, Bu4NClO4
Page 10: R1 R2 E1 E2 H H 0.35 0.77 Me Me 0.26 0.62 OMe OMe 0.44 0.68 SMe SMe 0.51 0.78 (CH=CH)2 (CH=CH)2 0.62 0.94 SMe H 0.44 0.77 SMe CO2Me 0.83 1.22 SMe CN 1.04 1.32 V vs. SCE, in PhCN, Bu4NClO4

cm2/s)

k>10-2

10-2 >k>10-4

10-4 > k

Page 11: R1 R2 E1 E2 H H 0.35 0.77 Me Me 0.26 0.62 OMe OMe 0.44 0.68 SMe SMe 0.51 0.78 (CH=CH)2 (CH=CH)2 0.62 0.94 SMe H 0.44 0.77 SMe CO2Me 0.83 1.22 SMe CN 1.04 1.32 V vs. SCE, in PhCN, Bu4NClO4

reversible)

k>10-2 cm/s)

irreversible) quasi-reversible)

k<10-4 cm/s)

Page 12: R1 R2 E1 E2 H H 0.35 0.77 Me Me 0.26 0.62 OMe OMe 0.44 0.68 SMe SMe 0.51 0.78 (CH=CH)2 (CH=CH)2 0.62 0.94 SMe H 0.44 0.77 SMe CO2Me 0.83 1.22 SMe CN 1.04 1.32 V vs. SCE, in PhCN, Bu4NClO4
Page 13: R1 R2 E1 E2 H H 0.35 0.77 Me Me 0.26 0.62 OMe OMe 0.44 0.68 SMe SMe 0.51 0.78 (CH=CH)2 (CH=CH)2 0.62 0.94 SMe H 0.44 0.77 SMe CO2Me 0.83 1.22 SMe CN 1.04 1.32 V vs. SCE, in PhCN, Bu4NClO4
Page 14: R1 R2 E1 E2 H H 0.35 0.77 Me Me 0.26 0.62 OMe OMe 0.44 0.68 SMe SMe 0.51 0.78 (CH=CH)2 (CH=CH)2 0.62 0.94 SMe H 0.44 0.77 SMe CO2Me 0.83 1.22 SMe CN 1.04 1.32 V vs. SCE, in PhCN, Bu4NClO4

-

Page 15: R1 R2 E1 E2 H H 0.35 0.77 Me Me 0.26 0.62 OMe OMe 0.44 0.68 SMe SMe 0.51 0.78 (CH=CH)2 (CH=CH)2 0.62 0.94 SMe H 0.44 0.77 SMe CO2Me 0.83 1.22 SMe CN 1.04 1.32 V vs. SCE, in PhCN, Bu4NClO4

Red Ox + ne-

CR, CO

DR, DO: R O

CR*:Red

Page 16: R1 R2 E1 E2 H H 0.35 0.77 Me Me 0.26 0.62 OMe OMe 0.44 0.68 SMe SMe 0.51 0.78 (CH=CH)2 (CH=CH)2 0.62 0.94 SMe H 0.44 0.77 SMe CO2Me 0.83 1.22 SMe CN 1.04 1.32 V vs. SCE, in PhCN, Bu4NClO4
Page 17: R1 R2 E1 E2 H H 0.35 0.77 Me Me 0.26 0.62 OMe OMe 0.44 0.68 SMe SMe 0.51 0.78 (CH=CH)2 (CH=CH)2 0.62 0.94 SMe H 0.44 0.77 SMe CO2Me 0.83 1.22 SMe CN 1.04 1.32 V vs. SCE, in PhCN, Bu4NClO4
Page 18: R1 R2 E1 E2 H H 0.35 0.77 Me Me 0.26 0.62 OMe OMe 0.44 0.68 SMe SMe 0.51 0.78 (CH=CH)2 (CH=CH)2 0.62 0.94 SMe H 0.44 0.77 SMe CO2Me 0.83 1.22 SMe CN 1.04 1.32 V vs. SCE, in PhCN, Bu4NClO4
Page 19: R1 R2 E1 E2 H H 0.35 0.77 Me Me 0.26 0.62 OMe OMe 0.44 0.68 SMe SMe 0.51 0.78 (CH=CH)2 (CH=CH)2 0.62 0.94 SMe H 0.44 0.77 SMe CO2Me 0.83 1.22 SMe CN 1.04 1.32 V vs. SCE, in PhCN, Bu4NClO4
Page 20: R1 R2 E1 E2 H H 0.35 0.77 Me Me 0.26 0.62 OMe OMe 0.44 0.68 SMe SMe 0.51 0.78 (CH=CH)2 (CH=CH)2 0.62 0.94 SMe H 0.44 0.77 SMe CO2Me 0.83 1.22 SMe CN 1.04 1.32 V vs. SCE, in PhCN, Bu4NClO4

HOMO LUMO

Page 21: R1 R2 E1 E2 H H 0.35 0.77 Me Me 0.26 0.62 OMe OMe 0.44 0.68 SMe SMe 0.51 0.78 (CH=CH)2 (CH=CH)2 0.62 0.94 SMe H 0.44 0.77 SMe CO2Me 0.83 1.22 SMe CN 1.04 1.32 V vs. SCE, in PhCN, Bu4NClO4

TCNQ

CN

CNNC

NCOO

S

S S

S

TTF

Page 22: R1 R2 E1 E2 H H 0.35 0.77 Me Me 0.26 0.62 OMe OMe 0.44 0.68 SMe SMe 0.51 0.78 (CH=CH)2 (CH=CH)2 0.62 0.94 SMe H 0.44 0.77 SMe CO2Me 0.83 1.22 SMe CN 1.04 1.32 V vs. SCE, in PhCN, Bu4NClO4

TTF TCNQ

+•-e

+e +e

-e

-

- -

•

-e

+e

-e

+e

TCNQ TCNQ-• TCNQ2-

+ +

CNNC

NC CN

S

SS

S

CNNC

NC CN

CNNC

NC CN

S

SS

S S

SS

S

TTF TTF+• TTF2+

Page 23: R1 R2 E1 E2 H H 0.35 0.77 Me Me 0.26 0.62 OMe OMe 0.44 0.68 SMe SMe 0.51 0.78 (CH=CH)2 (CH=CH)2 0.62 0.94 SMe H 0.44 0.77 SMe CO2Me 0.83 1.22 SMe CN 1.04 1.32 V vs. SCE, in PhCN, Bu4NClO4

p-

R E1 E2

H -0.37 -1.15

Me -0.55 -1.50

OMe -0.36 -1.23

SMe -0.29 -1.23

Br -0.14 -0.80

Cl -0.03 -0.76

O

OR

R

2,3-

Page 24: R1 R2 E1 E2 H H 0.35 0.77 Me Me 0.26 0.62 OMe OMe 0.44 0.68 SMe SMe 0.51 0.78 (CH=CH)2 (CH=CH)2 0.62 0.94 SMe H 0.44 0.77 SMe CO2Me 0.83 1.22 SMe CN 1.04 1.32 V vs. SCE, in PhCN, Bu4NClO4

p-

R1 R2 E1 E2

H H -0.32 -1.07

Me Me -0.69 -1.51

OMe OMe -0.47 -1.24

I -0.14 -0.80

Br Br +0.21 -0.56

Cl Cl +0.22 -0.58

F F +0.21 -0.67

Cl CN +0.62 -0.11

O

OR2

R2R1

R1

V vs. Ag/AgCl, in CH2Cl2, Bu4NBF4

Page 25: R1 R2 E1 E2 H H 0.35 0.77 Me Me 0.26 0.62 OMe OMe 0.44 0.68 SMe SMe 0.51 0.78 (CH=CH)2 (CH=CH)2 0.62 0.94 SMe H 0.44 0.77 SMe CO2Me 0.83 1.22 SMe CN 1.04 1.32 V vs. SCE, in PhCN, Bu4NClO4

TTF

R1 R2 E1 E2

H H 0.35 0.77

Me Me 0.26 0.62

OMe OMe 0.44 0.68

SMe SMe 0.51 0.78

(CH=CH)2 (CH=CH)2 0.62 0.94

SMe H 0.44 0.77

SMe CO2Me 0.83 1.22

SMe CN 1.04 1.32

V vs. SCE, in PhCN, Bu4NClO4

S

S S

S R2

R2R1

R1

Page 26: R1 R2 E1 E2 H H 0.35 0.77 Me Me 0.26 0.62 OMe OMe 0.44 0.68 SMe SMe 0.51 0.78 (CH=CH)2 (CH=CH)2 0.62 0.94 SMe H 0.44 0.77 SMe CO2Me 0.83 1.22 SMe CN 1.04 1.32 V vs. SCE, in PhCN, Bu4NClO4

1,3- [5]

S

SS

S

SS

SS

SS

SS

SS

S

S

SS

S

SO

SS

S

S

SS

S

SSS

Page 27: R1 R2 E1 E2 H H 0.35 0.77 Me Me 0.26 0.62 OMe OMe 0.44 0.68 SMe SMe 0.51 0.78 (CH=CH)2 (CH=CH)2 0.62 0.94 SMe H 0.44 0.77 SMe CO2Me 0.83 1.22 SMe CN 1.04 1.32 V vs. SCE, in PhCN, Bu4NClO4

1,3- [5]

SS

S

S

SS

S

SSS

R

R

RR

R

RR

R

R

R

SS

S

S

SS

S

SSS

R

R

RR

R

RR

R

R

R

+

+

+

+

+

+

+

+

+

5 5

Page 28: R1 R2 E1 E2 H H 0.35 0.77 Me Me 0.26 0.62 OMe OMe 0.44 0.68 SMe SMe 0.51 0.78 (CH=CH)2 (CH=CH)2 0.62 0.94 SMe H 0.44 0.77 SMe CO2Me 0.83 1.22 SMe CN 1.04 1.32 V vs. SCE, in PhCN, Bu4NClO4

S

S

S

S

S

S

S

S

SS

S

S

SS

S

SO

SS

S

S

SS

S

SSS

R

R

R

RR

R

R

R

R

R

R

RR

R

R

RR

R

RR

R

RR

R

R

R

SS

S

S

SS

S

S

R

R

R

RR

R

R

R

SS

S

S

SS

S

SOH

R

R

R

RR

R

R

R

SS

S

S

SS

S

S

R

RR

R

R

R

H

1

+

+

+

+

+

+

+

+

+

+

+ +

+

5

+

+

+

+

+

+

+

+

+

+

+

+

7

2R = -(CH=CH)2-

+1.59 V

+1.22 V

+0.63V

R

R

+0.36V

+0.70V +0.37V

Page 29: R1 R2 E1 E2 H H 0.35 0.77 Me Me 0.26 0.62 OMe OMe 0.44 0.68 SMe SMe 0.51 0.78 (CH=CH)2 (CH=CH)2 0.62 0.94 SMe H 0.44 0.77 SMe CO2Me 0.83 1.22 SMe CN 1.04 1.32 V vs. SCE, in PhCN, Bu4NClO4

HOMO LUMO

Page 30: R1 R2 E1 E2 H H 0.35 0.77 Me Me 0.26 0.62 OMe OMe 0.44 0.68 SMe SMe 0.51 0.78 (CH=CH)2 (CH=CH)2 0.62 0.94 SMe H 0.44 0.77 SMe CO2Me 0.83 1.22 SMe CN 1.04 1.32 V vs. SCE, in PhCN, Bu4NClO4

S

S

S

S

S

S

S

S

S

S S

S

Pb(OAc)4

CF3CO2H54%

S

S S

S

S

S

S

S -e

+e

-e

+eS

S

S

S +.

S

S

S

S 2+

++S

SS

S

TTF2+

-e

+e

-e

+e•+

S

SS

S

TTF+.TTF

Page 31: R1 R2 E1 E2 H H 0.35 0.77 Me Me 0.26 0.62 OMe OMe 0.44 0.68 SMe SMe 0.51 0.78 (CH=CH)2 (CH=CH)2 0.62 0.94 SMe H 0.44 0.77 SMe CO2Me 0.83 1.22 SMe CN 1.04 1.32 V vs. SCE, in PhCN, Bu4NClO4

S

S S

SS

S S

S S

S S

S

E1 = -0.11, E2 = -0.44 V E = 0.00 V E = 0.40 V

Page 32: R1 R2 E1 E2 H H 0.35 0.77 Me Me 0.26 0.62 OMe OMe 0.44 0.68 SMe SMe 0.51 0.78 (CH=CH)2 (CH=CH)2 0.62 0.94 SMe H 0.44 0.77 SMe CO2Me 0.83 1.22 SMe CN 1.04 1.32 V vs. SCE, in PhCN, Bu4NClO4

X

S

S S

S

Page 33: R1 R2 E1 E2 H H 0.35 0.77 Me Me 0.26 0.62 OMe OMe 0.44 0.68 SMe SMe 0.51 0.78 (CH=CH)2 (CH=CH)2 0.62 0.94 SMe H 0.44 0.77 SMe CO2Me 0.83 1.22 SMe CN 1.04 1.32 V vs. SCE, in PhCN, Bu4NClO4

1,3- [6]

S

S

S

S

Br

Br

Ni(PPH3)4/Zn-Cu

R

R

R

R

SS

S

S

S

S

S S

S

S

S

S

3b,c

R = CO2Me, 2R = -(CH=CH)2

R

R

R

R

R R

R

R

R

R

RR

DMF

Page 34: R1 R2 E1 E2 H H 0.35 0.77 Me Me 0.26 0.62 OMe OMe 0.44 0.68 SMe SMe 0.51 0.78 (CH=CH)2 (CH=CH)2 0.62 0.94 SMe H 0.44 0.77 SMe CO2Me 0.83 1.22 SMe CN 1.04 1.32 V vs. SCE, in PhCN, Bu4NClO4

1,3- [6]

Page 35: R1 R2 E1 E2 H H 0.35 0.77 Me Me 0.26 0.62 OMe OMe 0.44 0.68 SMe SMe 0.51 0.78 (CH=CH)2 (CH=CH)2 0.62 0.94 SMe H 0.44 0.77 SMe CO2Me 0.83 1.22 SMe CN 1.04 1.32 V vs. SCE, in PhCN, Bu4NClO4

1,3- [6]

(3) (3’)

1,3-


APEC SME Crisis Management Center APEC SME Economic Crisis

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