Effect of end groups on the band gap of donor-acceptor based small molecules containing diketopyrrolopyrrole

Article abstract of DOI:10.3987/COM-17-13685

(Acceptor-donor-acceptor type compounds 5,5′-(4,4′-(2,5-bis(2-octyldodecyl)-3,6-dioxo-2,3,5,6-tetrahydropyrrolo[3,4-c]pyrrole-1,4-diyl)bis(4,1-phenylene))dithiophene-2-carbonitrile (DPPTCN), 4′,4″-(2,5-bis(2-octyldodecyl)-3,6-dioxo-2,3,5,6-tetrahydropyrrolo[3,4-c]pyrrole-1,4-diyl)dibiphenyl-4-carbonitrile (DPPPhCN), 2,2′-(5,5′-(4,4′-(2,5-bis(2-octyldodecyl)-3,6-dioxo-2,3,5,6-tetra-hydropyrrolo[3,4-c]pyrrole-1,4-diyl)bis(4,1-phenylene))bis(thiophene-5,2-diyl))-bis(methan-1-yl-1-ylidene)dimalononitrile (DPPT2CN), 2,2′-(4′,4″-(2,5-bis(2-octyldodecyl)-3,6-dioxo-2,3,5,6-tetrahydropyrrolo[3,4-c]pyrrole-1,4-diyl)bis(biphenyl-4′,4-diyl))bis(methan-1-yl-1-ylidene)dimalononitrile (DPPPh2CN) were designed and synthesized. All the compounds have central diketopyrrolopyrrole common acceptor unit, the donor groups differ either thiophene or phenyl group and the terminal end groups are differ either nitrile or dicyanovinylene groups. In order to study the relationship between chemical structure and properties, their optical, thermal and electrochemical properties were investigated. Thermal properties indicate that all the compounds have high thermal stability. Among DPPT2CN with thiophene groups as donor and dicyanovinylene as acceptor has shown lowest LUMO energy level of -3.77 eV and low HOMO-LUMO band gap 1.86 eV.

Full text of DOI:10.3987/COM-17-13685

EFFECT OF END GROUPS ON THE BAND GAP OF DONOR-ACCEPTOR BASED
SMALL MOLECULES CONTAINING DIKETOPYRROLOPYRROLE
Jin-Hee Han,a,1 Hun-Min Kang,a,1 Dong Jin Song,a Baji Shaik,b Yu Mi Heo,b Hye Jin
Chung,b and Seung-Mann Paekb,*
aDepartment of Chemistry, Research Institute of Natural Science (RINS),
Graduate School for Molecular Materials and Nanochemistry, Gyeongsang
National University, Jinju 660-701, Korea
bCollege of Pharmacy and Research Institute of Pharmaceutical Sciences,
Gyeongsang National University, Jinju daero, Jinju, Gyeongnam 660-701, Korea.
*E-mail: million@gnu.ac.kr; Tel.: +82 55 772 2424; Fax: +82 55 772 2429
Figure S1. 1H-NMR spectrum of DPPTCN.
Figure S2. 13C-NMR spectrum of DPPTCN.
Figure S3. HRMS (FAB) spectrum of DPPTCN.
Figure S4. 1H-NMR spectrum of DPPPhCN.
Figure S5. 13C-NMR spectrum of DPPPhCN
Figure S6. HRMS (FAB) spectrum of DPPPhCN.
Figure S7. 1H-NMR spectrum of compound 9.
Figure S8. 13C-NMR spectrum of compound 9.
Figure S9. HRMS (FAB) spectrum of compound 9.
Figure S10. 1H-NMR spectrum of compound 11.
Figure S11. 13C-NMR spectrum of compound 11.
Figure S12. HRMS (FAB) spectrum of compound 11.
Figure S13. 1H-NMR spectrum of DPPT2CN.
Figure S14. 13C-NMR spectrum of DPPT2CN.
1

Figure S15. HRMS (FAB) spectrum of DPPT2CN.
Figure S16. 1H-NMR spectrum of DPPPh2CN.
Figure S17. 13C-NMR spectrum of DPPPh2CN.
Figure S18. HRMS (FAB) spectrum of DPPPh2CN.
2

C10H21
C8H17
N
O
NC
S
CN
S
O
N
C8H17
C10H21
DPPTCN
Figure S1. 1H-NMR spectrum of DPPTCN.
C10H21
C8H17
N
O
NC
S
CN
S
O
N
C8H17
C10H21
DPPTCN
Figure S2. 13C-NMR spectrum of DPPTCN.
3

C10H21
C8H17
N
O
NC
S
CN
S
O
N
C8H17
C10H21
DPPTCN
Figure S3. HRMS (FAB) spectrum of DPPTCN.
4

C10H21
C8H17
N
O
NC
CN
O
N
C8H17
C10H21
DPPPhCN
Figure S4. 1H-NMR spectrum of DPPPhCN.
C10H21
C8H17
N
O
NC
CN
O
N
C8H17
C10H21
DPPPhCN
Figure S5. 13C-NMR spectrum of DPPPhCN
5

C10H21
C8H17
N
O
NC
CN
O
N
C8H17
C10H21
DPPPhCN
Figure S6. HRMS (FAB) spectrum of DPPPhCN.
6

C10H21
C8H17
N
O
S
OHC
CHO
S
O
N
C8H17
C10H21
9
Figure S7. 1H-NMR spectrum of compound 9.
C10H21
C8H17
N
O
S
OHC
CHO
S
O
N
C8H17
C10H21
9
Figure S8. 13C-NMR spectrum of compound 9.
7

C10H21
C8H17
N
O
S
OHC
CHO
S
O
N
C8H17
C10H21
9
Figure S9. HRMS (FAB) spectrum of compound 9.
8

C10H21
C8H17
N
O
OHC
CHO
O
N
C8H17
C10H21
11
Figure S10. 1H-NMR spectrum of compound 11.
C10H21
C8H17
N
O
OHC
CHO
O
N
C8H17
C10H21
11
Figure S11. 13C-NMR spectrum of compound 11.
9

C10H21
C8H17
N
O
OHC
CHO
O
N
C8H17
C10H21
11
Figure S12. HRMS (FAB) spectrum of compound 11.
10

C10H21
C8H17
N
NC
NC
O
S
CN
CN
S
O
N
C8H17
C10H21
DPPT2CN
Figure S13. 1H-NMR spectrum of DPPT2CN.
C10H21
C8H17
N
NC
NC
O
S
CN
CN
S
O
N
C8H17
C10H21
DPPT2CN
Figure S14. 13C-NMR spectrum of DPPT2CN.
11

C10H21
C8H17
N
NC
NC
O
S
CN
CN
S
O
N
C8H17
C10H21
DPPT2CN
Figure S15. HRMS (FAB) spectrum of DPPT2CN.
12

C10H21
CN
C8H17
NC
N
O
O
N
CN
C8H17
NC
C10H21
DPPPh2CN
Figure S16. 1H-NMR spectrum of DPPPh2CN.
C10H21
CN
C8H17
NC
N
O
O
N
CN
C8H17
NC
C10H21
DPPPh2CN
Figure S17. 13C-NMR spectrum of DPPPh2CN.
13

C10H21
CN
C8H17
NC
N
O
O
N
CN
C8H17
NC
C10H21
DPPPh2CN
Figure S18. HRMS (FAB) spectrum of DPPPh2CN.
14