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Supporting Information for

Isoindigo-Based Small Molecules for Solution-Processed Organic

Photovoltaic Devices: Electron Donating Effect of Donor Group

on Photo-Physical Properties and Device Performance

Walaa Elsawy

1,2,7, Chang-Lyoul Lee

3,*, Shinuk Cho

4, Seung-Hwan Oh

5, Seung-Hyeon

Moon,6

Ahmed Elbarbary 7

and Jae-Suk Lee1,2,

*

1Department of Nanobio Materials and Electronics and School of Material Science and Engineering, 2Research Institute for

Solar and Sustainable Energies (RISE), 3Advanced Photonics Research Institute (APRI), 6School of Environmental Science

and Engineering, Gwangju Institute of Science and Technology (GIST), Gwangju 500-712, Republic of Korea 4Departments of Physics and EHSRC, University of Ulsan, Ulsan 680-749, Republic of Korea 5Radiation Research Division for Industry & Environment, Korea Atomic Energy Research Institute (KAERI), 580-185,

Republic of Korea 7 Department of Chemistry, Faculty of Science, Tanta University, Tanta 31527, Egypt

Electronic Supplementary Material (ESI) for Physical Chemistry Chemical PhysicsThis journal is © The Owner Societies 2013

Fig. S1 PL spectra of isoindigo donor-acceptor-donor (D-A-D) small molecules in solution

state. The chloroform was used as solvent. The solution concentration was 10-5

mol.

Fig. S2 Thermo Gravimetric Analysis (TGA) curves of isoindigo donor-acceptor-donor (D-

A-D) small molecules.

500 600 700 800 900 1000

IDED

IDHT

IDT

ID2T

ID3TP

L i

ne

nis

ty (

a.u

.)

Wavelength (nm)

100 200 300 400 500 6000

20

40

60

80

100

Weig

ht

(%)

Temperature (oC)

IDED

IDHT

IDT

ID2T

ID3T


Fig. S3 (a) Current density versus voltage characteristics of ITO/PEDOT:PSS/

ID2T:PC70BM/TiO2/Al organic photovoltaic devices with different donor and acceptor ratio

without DIO. (b) Current density versus voltage characteristics of ITO/PEDOT:PSS/

ID2T:PC70BM(70:30)/TiO2/Al organic photovoltaic devices with different DIO content.

-0.2 0.0 0.2 0.4 0.6 0.8 1.0-8

-6

-4

-2

0

2

4

Cu

rren

t d

en

sit

y (

mA

/cm

2)

Voltage (V)

ID2T:PC70

BM (50:50)

ID2T:PC70

BM (60:40)

ID2T:PC70

BM (70:30)

ID2T:PC70

BM (80:20)

(a)

-0.2 0.0 0.2 0.4 0.6 0.8 1.0-8

-6

-4

-2

0

2

4

Cu

rre

nt

de

ns

ity

(m

A/c

m2)

Voltage (V)

ID2T:PC70

BM (0.05% DIO)

ID2T:PC70

BM (0.1% DIO)

ID2T:PC70

BM (0.15% DIO)

ID2T:PC70

BM (0.2% DIO)

(b)


Table S1 Photovoltaic performance of ITO/PEDOT:PSS/ID2T:PC70BM/TiO2/Al organic

photovoltaic devices with different donor and acceptor ratio (without DIO) and DIO content.

The ID2T and PC70BM ratio was fixed with 70:30 in photovoltaic devices with different DIO

content.

Donor : acceptor ratio Jsc(mA/cm2) Voc(V) FF (%) PCE (%)

50:50 4.42 0.92 29.1 1.19

60:40 6.12 0.93 35.4 2.04

70:30 7.0 0.93 36.3 2.30

80:20 4.86 0.88 34.8 1.49

DIO content (%)

0.05 5.93 0.85 31.7 1.59

0.1 6.58 0.93 42.8 2.60

0.15 5.48 0.93 44.6 2.26

0.2 2.77 0.80 40.9 0.90


Fig. S4 (a) Current density versus voltage characteristics of ITO/PEDOT:PSS/IDHT:

PC70BM (70:30)/TiO2/Al and ITO/PEDOT:PSS/IDED:PC70BM (70:30)/TiO2/Al organic

photovoltaic devices with 0.1% DIO.

-0.2 0.0 0.2 0.4 0.6 0.8-0.4

-0.2

0.0

0.2

0.4

0.6

IDED:PC70

BM

IDHT:PC70

BM

C

urre

nt

de

ns

ity

(m

A/c

m2)

Voltage (V)


Fig. S5 Output and transfer characteristics of OTFTs based on the isoindigo donor-acceptor-

donor (D-A-D) small molecules. (a) IDED, (b) IDHT, (c) IDT, (d) ID2T and (e) ID3T.

(a)

-60 -40 -20 0 20

10-12

10-11

10-10

10-9

10-8

Vds

=-60V

| I d

s | (

A)

Vgs

(V)-60 -40 -20 0

-10

-8

-6

-4

-2

0

Id

s (

nA

)

Vds

(V)

-60 -40 -20 0 200.00

0.02

0.04

0.06

0.08

0.10

0.12

Vt=-20V

(| I

ds |)1

/2 (

x10

-3 A

1/2)

Vgs

(V)

(b)

-60 -40 -20 0-0.20

-0.15

-0.10

-0.05

0.00

Id

s (A

)

Vds

(V)-60 -40 -20 0 20

0.0

0.1

0.2

0.3

0.4

0.5

0.6

V

t=-21V

(| I

ds |)1

/2 (

x10

-3 A

1/2)

Vgs

(V)-60 -40 -20 0 20

10-12

10-11

10-10

10-9

10-8

10-7

10-6

Vds

=-60V

| I d

s | (

A)

Vgs

(V)


(c)

-60 -40 -20 0-3.0

-2.5

-2.0

-1.5

-1.0

-0.5

0.0

Id

s (A

)

Vds

(V)-60 -40 -20 0 20

0.0

0.5

1.0

1.5

2.0

2.5

Vt=-18V

(| I

ds |)1

/2 (

x10

-3 A

1/2)

Vgs

(V)-60 -40 -20 0 20

10-12

10-11

10-10

10-9

10-8

10-7

10-6

10-5

Vds

=-60V

| I d

s | (

A)

Vgs

(V)

(d)

-60 -40 -20 0-10

-8

-6

-4

-2

0

Id

s (A

)

Vds

(V)-60 -40 -20 0 200

1

2

3

4

Vt=-16V

(| I

ds |)1

/2 (

x10

-3 A

1/2)

Vgs

(V)-60 -40 -20 0 20

10-12

10-11

10-10

10-9

10-8

10-7

10-6

10-5

| I d

s | (

A)

Vgs

(V)

Vds

=-60V

(e)

-60 -40 -20 0-0.14

-0.12

-0.10

-0.08

-0.06

-0.04

-0.02

0.00

Id

s (A

)

Vds

(V)-60 -40 -20 0 20

10-12

10-11

10-10

10-9

10-8

10-7

10-6

| I d

s | (

A)

Vgs

(V)

Vds

=-60V

-60 -40 -20 0 20

0.0

0.1

0.2

0.3

0.4

0.5

(| I

ds |)1

/2 (

x10

-3 A

1/2)

Vgs

(V)

Vt=-26V


Table S2 Field-effect charge transport properties of isoindigo donor-acceptor-donor (D-A-D)

small molecules. Vds is -60V.

Active layer h(cm2/(Vs)) Ion/Ioff Vt (V)

IDED 3.2 10-5

4.5 103 -20

IDHT 1.1 10-3

5.7 104 -21

IDT 1.4 10-2

1.3 106 -18

ID2T 3.6 10-2

3.4 106 -16

ID3T 9.7 10-4

1.0 105 -26


Fig. S6 Transfer curves of OTFTs based on the isoindigo donor-acceptor-donor (D-A-D)

small molecules:PC70BM (70:30) film. (a) IDT (b) IDHT and IDED.

(a)

-60 -40 -20 0 20 40 60

10-9

10-8

10-7

10-6

p-type operation

Vds

= -60 V

n-type operation

Vds

= 60 VIDT:PC

71BM

| I d

s | (

A)

Vgs

(V)

w/o DIO

w/ DIO

w/o DIO

w/ DIO

(b)

-60 -40 -20 0 20 40 6010

-11

10-10

10-9

10-8

n-type operation

Vds

= 60 V

p-type operation

Vds

= -60 V

| I d

s | (

A)

Vgs

(V)

IDED

IDHT


Table S3 Field-effect charge transport properties of isoindigo donor-acceptor-donor (D-A-D)

small molecules:PC70BM (70:30). Vds is 60V.

Active layer e(cm2/(Vs))

a h(cm

2/(Vs))

a e(cm

2/(Vs))

b h(cm

2/(Vs))

b

IDED:PC70BM 4.62 10-5

2.09 10-5

N/Ac N/A

c

IDHT:PC70BM 5.19 10-5

2.96 10-5

N/Ac N/A

c

IDT:PC70BM 6.15 10-3

1.37 10-4

7.80 10-3

8.76 10-3

aElectron and hole mobility of photo-active layer without DIO,

bElectron and hole mobility of

active photo-layer with 0.1% DIO, cNot available, there was no additive effect on the

IDED:PC70BM and IDHT:PC70BM films.


Fig. S7

1H and

13C NMR spectrum of 6, 6’-dihydrothieno[3,4-b][1,4]dioxin-2-yl-N,N’-(2-

ethylhexyl)-isoindigo (IDED) in CDCl3.

N

N

O

OS

S

N

NO

OS

S

OO

O O


Fig. S8 1H and

13C NMR spectrum of 6,6’-dihexylthiophen-2-yl-N,N’-(2-ethylhexyl)-

isoindigo (IDHT) in CDCl3.

Fig. S9 1H and

13C NMR of spectrum of 6, 6’-thiophen-2-yl-N,N’-(2-ethylhexyl)-isoindigo

(IDT) in CDCl3.

Fig. S10

1H and

13C NMR spectrum of 6, 6’-bithiophen-2-yl-N,N’-(2-ethylhexyl)-isoindigo

(ID2T) in CDCl3.

N

NO

OS

S

N

NO

OS

S

S

S


Fig. S11

1H and

13C NMR spectrum of 6, 6’-terthiophen-2-yl-N,N’-(2-ethylhexyl)-isoindigo

(ID3T) in CDCl3.

N

NO

OS

S

S

S

S

S


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