Microwave Synthesis of Thionated Naphthalene Diimide-Based Small Molecules and Polymers
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1 Supporting Information for Microwave Synthesis of Thionated Naphthalene Diimide-Based Small Molecules and Polymers Paniz Pahlavanlu, Andrew J. Tilley, Bryony T. McAllister, and Dwight S. Seferos* Department of Chemistry, University of Toronto 80 St. George Street, Toronto, Ontario, M5S 3H6, Canada * Table of Contents 1. Synthesis of Parent Compounds 1.1 Substrate Scope S4 1.2 Representative Synthetic Schemes S5 2. Microwave Thionation 2.1 Supplementary Kinetic Studies S6 2.2 Post-Polymerization Thionation S Synthetic Scheme S Photographs and Optical Micrographs S7 3. Physical Characterization 3.1 Nuclear Magnetic Resonance Spectra S8 3.2 Thermogravimetric Analysis Plots S Infrared Spectra S34 4. Optical Characterization 4.1 Optical Absorption Spectra S Photoluminescence Spectra S36 5. Computational Data 5.1 Optimized Geometries and HOMO/LUMO Visualizations S Optimized Geometry Data S Br-TNDIT-Br (Me) S S1 Br-TNDIT-Br (Me) S trans-s2 Br-TNDIT-Br (Me) S41 Pahlavanlu, P. et al. S1
2 List of Schemes, Figures, and Tables Figure S1. Chemical structures and abbreviations of parent compounds. S4 Scheme S1. Synthesis of Br-TNDIT-Br (2-OD). S5 Scheme S2. Synthesis of NDI (2-OD). S5 Figure S2. Microwave thionation kinetics of Br-TNDIT-Br (2-OD) using 0.5 mol. eq. Lawesson s reagent at temperatures ranging from ºC. S6 Scheme S3. Microwave post-polymerization thionation of PNDIT2. S7 Figure S3. Photographs and optical micrographs of P100-PNDIT2. S7 Figure S4. a) 1 H NMR and b) 13 C NMR spectra of NDI (2-OD). S8 Figure S5. a) 1 H NMR and b) 13 C NMR spectra of Br-NDI-Br (2-OD). S9 Figure S6. a) 1 H NMR and b) 13 C NMR spectra of Br-NDI-Br (3-HU). S10 Figure S7. a) 1 H NMR and b) 13 C NMR spectra of TNDIT (2-OD). S11 Figure S8. a) 1 H NMR and b) 13 C NMR spectra of TNDIT (3-HU). S12 Figure S9. a) 1 H NMR and b) 13 C NMR spectra of SeNDISe (2-OD). S13 Figure S10. a) 1 H NMR and b) 13 C NMR spectra of Br-TNDIT-Br (2-OD). S14 Figure S11. a) 1 H NMR and b) 13 C NMR spectra of Br-TNDIT-Br (3-HU). S15 Figure S12. a) 1 H NMR and b) 13 C NMR spectra of Br-SeNDISe-Br (2-OD). S16 Figure S13. a) 1 H NMR and b) 13 C NMR spectra of S1 Br-TNDIT-Br (2-OD). S17 Figure S14. a) 1 H NMR and b) 13 C NMR spectra of S1 Br-TNDIT-Br (3-HU). S18 Figure S15. a) 1 H NMR and b) 13 C NMR spectra of S1 Br-SeNDISe-Br (2-OD). S19 Figure S16. a) 1 H NMR and b) 13 C NMR spectra of trans-s2 Br-TNDIT-Br (2-OD). S20 Figure S17. a) 1 H NMR and b) 13 C NMR spectra of trans-s2 Br-TNDIT-Br (3-HU). S21 Figure S18. a) 1 H NMR and b) 13 C NMR spectra of trans-s2 Br-SeNDISe-Br (2-OD). S22 Figure S19. COSY NMR spectrum of Br-TNDIT-Br (2-OD). S23 Figure S20. COSY NMR spectrum of S1 Br-TNDIT-Br (2-OD). S24 Figure S21. COSY NMR spectrum of trans-s2 Br-TNDIT-Br (2-OD). S25 Figure S22. COSY NMR spectrum of Br-TNDIT-Br (3-HU). S26 Figure S23. COSY NMR spectrum of S1 Br-TNDIT-Br (3-HU). S27 Figure S24. COSY NMR spectrum of trans-s2 Br-TNDIT-Br (3-HU). S28 Figure S25. COSY NMR spectrum of Br-SeNDISe-Br (2-OD). S29 Figure S26. COSY NMR spectrum of S1 Br-SeNDISe-Br (2-OD). S30 Figure S27. COSY NMR spectrum of trans-s2 Br-SeNDISe-Br (2-OD). S31 Figure S28. Low field portion of HMBC NMR spectra of a) P, b) S1, and c) trans-s2 Br-TNDIT- Br (3-HU). S32 Figure S29. Low field portion of HMBC NMR spectra of a) P, b) S1, and c) trans-s2 Br-SeNDISe- Br (2-OD). S32 Figure S30. Thermogravimetric analysis plots of P, S1, and trans-s2 Br-TNDIT-Br (2-OD). S33 Figure S31. DFT calculated vibrational frequency spectra. S34 Figure S32. Infrared spectra of a) P, b) S1, and c) trans-s2 Br-TNDIT-Br (3-HU). S34 Pahlavanlu, P. et al. S2
3 Figure S33. Infrared spectra of a) P, b) S1, and c) trans-s2 Br-SeNDISe-Br (2-OD). S34 Figure S34. Normalized optical absorption spectra of a) P, b) S1, c) trans-s2 Br-TNDIT-Br (2- OD) in cyclohexane, CHCl 3, and tetrahydrofuran. S35 Figure S35. Normalized optical absorption spectra of a) P, S1, and trans-s2 Br-TNDIT-Br (3- HU) and b) P, S1, and trans-s2 Br-SeNDISe-Br (2-OD) in CHCl 3. S35 Figure S36. Photoluminescence spectra of P, S1, and trans-s2 of a) Br-TNDIT-Br (2-OD), b) Br- TNDIT-Br (3-HU), and c) Br-SeNDISe-Br (2-OD) in CHCl 3 (λ ex = 450 nm). S36 Figure S37. Optimized geometries and HOMO/LUMO visualizations of P, S1, and trans-s2 Br- TNDIT-Br (Me) calculated using DFT. S36 Table S1. Optimized geometry coordinates of Br-TNDIT-Br (Me). S37 Table S2. Optimized geometry coordinates of S1 Br-TNDIT-Br (Me). S39 Table S3. Optimized geometry coordinates of trans-s2 Br-TNDIT-Br (Me). S41 Pahlavanlu, P. et al. S3
4 1. Synthesis of Parent Compounds 1.1 Substrate Scope Figure S1. Chemical structures and abbreviations of parent compounds. Pahlavanlu, P. et al. S4
5 1.2 Representative Synthetic Schemes Scheme S1. Synthesis of Br-TNDIT-Br (2-OD). *Relative to 50% 2,6-BrNDABr in starting material. Scheme S2. Synthesis of NDI (2-OD). Pahlavanlu, P. et al. S5
6 2. Microwave Thionation 2.1 Supplementary Kinetic Studies Figure S2. Microwave thionation kinetics of Br-TNDIT-Br (2-OD) using 0.5 mol. eq. Lawesson s reagent at temperatures ranging from ºC, as measured through 1 H NMR analysis of naphthyl core protons. Pahlavanlu, P. et al. S6
7 2.2 Post-Polymerization Thionation Synthetic Scheme Scheme S3. Microwave post-polymerization thionation of PNDIT Photographs and Optical Micrographs Figure S3. a) Photograph of inverted microwave vial containing P100-PNDIT2 crude mixture, illustrating gel formation with extended thionation. b) Photograph of P100-PNDIT2 crude mixture swollen in toluene. c) Overlaid optical micrographs of purified and dried P100-PNDIT2, sliced with a razer blade. Pahlavanlu, P. et al. S7
8 3. Physical Characterization 3.1 Nuclear Magnetic Resonance Spectra Figure S4. a) 1 H NMR and b) 13 C NMR spectra of NDI (2-OD). Pahlavanlu, P. et al. S8
9 Figure S5. a) 1 H NMR and b) 13 C NMR spectra of Br-NDI-Br (2-OD). Pahlavanlu, P. et al. S9
10 Figure S6. a) 1 H NMR and b) 13 C NMR spectra of Br-NDI-Br (3-HU). Pahlavanlu, P. et al. S10
11 Figure S7. a) 1 H NMR and b) 13 C NMR spectra of TNDIT (2-OD). Pahlavanlu, P. et al. S11
12 Figure S8. a) 1 H NMR and b) 13 C NMR spectra of TNDIT (3-HU). Pahlavanlu, P. et al. S12
13 Figure S9. a) 1 H NMR and b) 13 C NMR spectra of SeNDISe (2-OD). Pahlavanlu, P. et al. S13
14 Figure S10. a) 1 H NMR and b) 13 C NMR spectra of Br-TNDIT-Br (2-OD). Pahlavanlu, P. et al. S14
15 Figure S11. a) 1 H NMR and b) 13 C NMR spectra of Br-TNDIT-Br (3-HU). Pahlavanlu, P. et al. S15
16 Figure S12. a) 1 H NMR and b) 13 C NMR spectra of Br-SeNDISe-Br (2-OD). Pahlavanlu, P. et al. S16
17 Figure S13. a) 1 H NMR and b) 13 C NMR spectra of S1 Br-TNDIT-Br (2-OD). Pahlavanlu, P. et al. S17
18 Figure S14. a) 1 H NMR and b) 13 C NMR spectra of S1 Br-TNDIT-Br (3-HU). Pahlavanlu, P. et al. S18
19 Figure S15. a) 1 H NMR and b) 13 C NMR spectra of S1 Br-SeNDISe-Br (2-OD). Pahlavanlu, P. et al. S19
20 Figure S16. a) 1 H NMR and b) 13 C NMR spectra of trans-s2 Br-TNDIT-Br (2-OD). Pahlavanlu, P. et al. S20
21 Figure S17. a) 1 H NMR and b) 13 C NMR spectra of trans-s2 Br-TNDIT-Br (3-HU). Pahlavanlu, P. et al. S21
22 Figure S18. a) 1 H NMR and b) 13 C NMR spectra of trans-s2 Br-SeNDISe-Br (2-OD). Pahlavanlu, P. et al. S22
23 Figure S19. COSY NMR spectrum of Br-TNDIT-Br (2-OD). Pahlavanlu, P. et al. S23
24 Figure S20. COSY NMR spectrum of S1 Br-TNDIT-Br (2-OD). Pahlavanlu, P. et al. S24
25 Figure S21. COSY NMR spectrum of trans-s2 Br-TNDIT-Br (2-OD). Pahlavanlu, P. et al. S25
26 Figure S22. COSY NMR spectrum of Br-TNDIT-Br (3-HU). Pahlavanlu, P. et al. S26
27 Figure S23. COSY NMR spectrum of S1 Br-TNDIT-Br (3-HU). Pahlavanlu, P. et al. S27
28 Figure S24. COSY NMR spectrum of trans-s2 Br-TNDIT-Br (3-HU). Pahlavanlu, P. et al. S28
29 Figure S25. COSY NMR spectrum of Br-SeNDISe-Br (2-OD). Pahlavanlu, P. et al. S29
30 Figure S26. COSY NMR spectrum of S1 Br-SeNDISe-Br (2-OD). Pahlavanlu, P. et al. S30
31 Figure S27. COSY NMR spectrum of trans-s2 Br-SeNDISe-Br (2-OD). Pahlavanlu, P. et al. S31
32 Figure S28. Low field portion of HMBC NMR spectra of a) P, b) S1, and c) trans-s2 Br-TNDIT- Br (3-HU). Through-bond coupling between naphthyl protons (H A, H A ) and neighbouring carbons reflects the proximity of these protons to either carbonyl or thionyl carbons (~160 ppm and 190 ppm, respectively). α-protons on the imide substituent (H B, H B ) serve as a frame of reference, since they are proximal to both carbonyl and thionyl carbons. Here, R = 2-hexyldecyl. Figure S29. Low field portion of HMBC NMR spectra of a) P, b) S1, and c) trans-s2 Br-SeNDISe- Br (2-OD). Through-bond coupling between naphthyl protons (H A, H A ) and neighbouring carbons reflects the proximity of these protons to either carbonyl or thionyl carbons (~160 ppm and 190 ppm, respectively). α-protons on the imide substituent (H B, H B ) serve as a frame of reference, since they are proximal to both carbonyl and thionyl carbons. Here, R = 1-octylundecyl. Pahlavanlu, P. et al. S32
33 3.2 Thermogravimetric Analysis Plots Figure S30. Thermogravimetric analysis plots of P, S1, and trans-s2 Br-TNDIT-Br (2-OD). Pahlavanlu, P. et al. S33
34 3.3 Infrared Spectra Figure S31. DFT calculated vibrational frequency spectra (left). Calculated frequencies of P, S1, and trans-s2 Br-TNDIT-Br (Me) correspond to characteristic carbonyl (C=O) and/or thionyl (C=S) stretches (right). Figure S32. Infrared spectra of a) P, b) S1, and c) trans-s2 Br-TNDIT-Br (3-HU), illustrating characteristic carbonyl (C=O) and/or thionyl (C=S) stretches. Figure S33. Infrared spectra of a) P, b) S1, and c) trans-s2 Br-SeNDISe-Br (2-OD), illustrating characteristic carbonyl (C=O) and/or thionyl (C=S) stretches. Pahlavanlu, P. et al. S34
35 4. Optoelectronic Characterization 4.1 Optical Absorption Spectra Figure S34. Normalized optical absorption spectra of a) P, b) S1, c) trans-s2 Br-TNDIT-Br (2- OD) in cyclohexane, CHCl 3, and tetrahydrofuran. Figure S35. Normalized optical absorption spectra of a) P, S1, and trans-s2 Br-TNDIT-Br (3- HU) and b) P, S1, and trans-s2 Br-SeNDISe-Br (2-OD) in CHCl 3. Pahlavanlu, P. et al. S35
36 4.2 Photoluminescence Spectra Figure S36. Photoluminescence spectra of P, S1, and trans-s2 of a) Br-TNDIT-Br (2-OD), b) Br- TNDIT-Br (3-HU), and c) Br-SeNDISe-Br (2-OD) in CHCl 3 (λ ex = 450 nm). 5. Computational Data 5.1 Optimized Geometries and HOMO/LUMO Visualizations Figure S37. Optimized geometries and HOMO/LUMO visualizations of P, S1, and trans-s2 Br- TNDIT-Br (Me) calculated using DFT (B3LYP functional, G(d) basis set). Pahlavanlu, P. et al. S36
37 5.2 Optimized Geometry Data Br-TNDIT-Br (Me) Method/Functional/Basis Set: DFT/B3LYP/6-311+G(d) Number of Imaginary Frequencies: 0 Total Energy of Optimized Structure: Hartrees Table S1. Optimized geometry coordinates of Br-TNDIT-Br (Me). Center Atomic Atomic Coordinates (Angstroms) Number Number Type X Y Z Pahlavanlu, P. et al. S37
38 Pahlavanlu, P. et al. S38
39 S1 Br-TNDIT-Br (Me) Method/Functional/Basis Set: DFT/B3LYP/6-311+G(d) Number of Imaginary Frequencies: 0 Total Energy of Optimized Structure: Hartrees Table S2. Optimized geometry coordinates of S1 Br-TNDIT-Br (Me). Center Atomic Atomic Coordinates (Angstroms) Number Number Type X Y Z Pahlavanlu, P. et al. S39
40 Pahlavanlu, P. et al. S40
41 trans-s2 Br-TNDIT-Br (Me) Method/Functional/Basis Set: DFT/B3LYP/6-311+G(d) Number of Imaginary Frequencies: 0 Total Energy of Optimized Structure: Hartrees Table S3. Optimized geometry coordinates of trans-s2 Br-TNDIT-Br (Me). Center Atomic Atomic Coordinates (Angstroms) Number Number Type X Y Z Pahlavanlu, P. et al. S41
42 Pahlavanlu, P. et al. S42
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