Novel electroluminescent donor-acceptors based on dibenzo[a,c]phenazine as
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1 Electronic Supplementary Material (ESI) for New Journal of Chemistry. This journal is The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2016 Novel electroluminescent donor-acceptors based on dibenzo[a,c]phenazine as hole transport materials for organic electronics Azam M. Shaikh, a Bharat K. Sharma, a Sajeev Chacko b and Rajesh M. Kamble *a a Department of Chemistry, University of Mumbai, Santacruz (East), Mumbai , India b Department of Physics, University of Mumbai, Santacruz (East), Mumbai , India * kamblerm@chem.mu.ac.in Supplementary Information 1
2 1) Photophysical data of compounds 2 6 in various solvents ) Emission of compounds ) Absorption and Emission spectra of compound 1 in toluene ) Absorption and Emission spectra of compound 2 6 in various solvents ) Tapping mode AFM topographical image of compound ) Cyclic voltammetry (CV) of compounds 2 6 in anhydrous dichloromethane ) Mass spectra of compound ) HRMS spectra of compounds ) FTIR Spectra of compounds ) 1 H and 13 C NMR spectra of compounds ) Optimized structures of compounds ) Cartesian coordinates of compounds a. Table S1. Cartesian coordinates of optimized structure of compound b. Table S2. Cartesian coordinates of optimized structure of compound c. Table S3. Cartesian coordinates of optimized structure of compound d. Table S4. Cartesian coordinates of optimized structure of compound e. Table S5. Cartesian coordinates of optimized structure of compound
3 1. Photophysical data of compounds 2 6 in various solvents a. Photophysical data of compounds 2 6 in cyclohexane. Compound λ emi a nm Stokes shift cm -1 E opt g (ev) a Recorded in10-5 M cyclohexane. φ F b. Photophysical data of compounds 2 6 in dichloromethane. Compound λ emi a nm Stokes shift cm -1 E opt g (ev) a Recorded in10-5 M dichloromethane. φ F 3
4 c. Photophysical data of compounds 2 6 in dimethyl sulfoxide (DMSO). Compound λ emi a nm Stokes shift cm -1 E opt g (ev) a Recorded in10-5 M dimethylsulfoxide. φ F 4
5 2. Emission of compounds 2 6 in various solvents under UV light (365 nm) Cyclohexane Dichloromethane Toluene Dimethyl sulfoxide 5
6 3. Absorption and emission spectra of compound 1in toluene Fig. S1 Absorption spectra of 1 in toluene Fig. S2 Emission spectra of 1 in toluene 6
7 4. Absorption and Emission spectra of compound 2 6 in various solvents a. Absorption spectra of compound 2 6 (a) Cyclohexane (b) Dichloromethane (c)dimethyl sulfoxide (d) Methanol 7
8 b. Emission spectra of compounds 2 6 (a) Toluene (b) Cyclohexane (c) Dichloromethane 8
9 (d) Dimethyl sulfoxide (e) Methanol 9
10 5. Tapping mode AFM topographical image of compound 2 6 AFM topographical image (2D) of compound 2 and 3 AFM topographical image 2D (left) and 3D (right) of compound 4 10
11 AFM topographical image 2D (left) and 3D (right) of compound 5 AFM topographical image 2D (left) and 3D (right) of compound 6 11
12 6. Cyclic Voltammogram of compounds
13 6. Mass spectra of compound 1 13
14 7. HRMS spectra of compounds 2 6. Fig. S3 HRMS Spectra of compound 2 14
15 Fig. S4 HRMS Spectra of compound 3 15
16 Fig. S5 HRMS Spectra of compound 4 16
17 Fig. S6 HRMS Spectra of compound 5 17
18 Fig. S7 HRMS Spectra of compound 6 18
19 8. FTIR Spectra of compounds 1 6 Fig. S8 FTIR Spectra of compound 1 Fig. S9 FTIR Spectra of compound 2 19
20 Fig. S10 FTIR Spectra of compound 3 Fig. S11 FTIR Spectra of compound 4 20
21 Fig. S12 FTIR Spectra of compound 5 Fig. S13 FTIR Spectra of compound 6 21
22 9. 1 H and 13 C NMR spectra of compounds 1 6 Fig. S14 1 H and 13 C NMR spectra of compound 1 in CDCl 3. 22
23 Fig. S15 1 H and 13 C NMR spectra of compound 2 in CDCl 3. 23
24 Fig. S16 1 H and 13 C NMR spectra of compound 3 in CDCl 3. 24
25 Fig. S17 1 H and 13 C NMR spectra of compound 4 in CDCl 3. 25
26 Fig. S18 1 H and 13 C NMR spectra of compound 5 in CDCl 3. 26
27 Fig. S19 1 H and 13 C NMR spectra of compound 6 in CDCl 3. 27
28 10. Optimized structures of compounds 2 6 Fig. S20 Optimized structure of compound 2 Fig. S21 Optimized structure of compound 3 28
29 Fig. S22 Optimized structure of compound 4 Fig. S23 Optimized structure of compound 5 29
30 Fig. S24 Optimized structure of compound 6 30
31 11. Cartesian coordinates of compounds of 2 6 Table S1. Cartesian coordinates of optimized structure of compound 2 Total energy: Hartrees Atom x y z C C C C C C C C C C C C C C N C C N C C C C N
32 N C C C C N C C C C C C C C C C C C C C C C C C C C C C C
33 C C C C C C C C C H H H H H H H H H H H H H H H H H H H H
34 H H H H H H H H H H H H H H H H H H H Table S2. Cartesian coordinates of optimized structure of compound 3 Total energy: Hartrees Atom x y z C C C C C
35 C C C C C C C C C N C C N C C C C N N C C C C N C C C C C
36 C C C C C C C C C C C C C C C C C C C C C C C C C C C C C
37 C C C C C C C C C C H H H H H H H H H H H H H H H H H H H
38 H H H H H H H H H H H H H H H H H H H H H H H H H H
39 Table S3. Cartesian coordinates of optimized structure of compound 4 Total energy: Hartrees Atom x y z C C C C C C C C C C C C C C N C C N C C C C N N C
40 C C C N C C C C C C C C C C C C C C C C C C C C C C C C C
41 C C C C C C C O O O O O H H H H H H H H H H H H H H H H H
42 H H H H H H H H H H H H H H H H C C C H H H H H H H H H O
43 C C C H H H H H H H H H Table S4. Cartesian coordinates of optimized structure of compound 5 Total energy: Hartrees Atom x y z C C C C C C C C C C C C
44 C C N C C N C C C C N N N C C C C C C C C C C C C C C C C
45 C C C C C C C C C C C C C C C C C C C C N N C C C C C C N
46 N C C C C C C N N C C C C C C H H H H H H H H H H H H H H
47 H H H H H H H H H H H H H H H H H H H H H H H H H H H H H
48 H H H H H H H H Table S5. Cartesian coordinates of optimized structure of compound 6 Total energy: Hartrees Atom x y z C C C C C C C C C C C C C C N C
49 C N C C C C N N N C C O C C C C O C C C C O C C H H H H H
50 H H H H H H H H H H H H H H H H H H H H H H H H H H H H
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