Synthesis, Solution, and Solid State Properties of Homological Dialkylated Naphthalene Diimides—A Systematic Review of Molecules for Next-Generation Organic Electronics
Abstract
:1. Introduction
2. Results and Discussion
2.1. Remarks on Synthesis: Towards Increasing the Synthesis Scale
2.2. UV-Vis Spectroscopy: Solubility of the NDIs
2.3. Characteristic Features of NMR Spectra of the Symmetrically N-Substituted NDIs
2.4. Effects of Alkyl Chain Length on FTIR Spectra of Solid NDIs
2.5. Crystal Structure of NDIs
2.6. Crystal Morphologies of NDIs
2.7. Thermal Properties of Solid NDIs
2.8. Field-Effect Electron Mobility
3. Materials and Methods
3.1. Materials
3.2. Synthesis
3.3. Preparation of Isotropic Samples
3.4. Infrared Spectroscopy
3.5. UV-Vis Spectroscopy and Solubility Studies
3.6. NMR Spectroscopy
3.7. Thermogravimetric Analysis and Differential Scanning Calorimetry
3.8. Polarized Optical Microscopy
3.9. X-ray Diffraction Measurements
3.10. Determination of Field-Effect Electron Mobility
4. Conclusions
Supplementary Materials
Author Contributions
Funding
Institutional Review Board Statement
Informed Consent Statement
Data Availability Statement
Acknowledgments
Conflicts of Interest
References
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Yield [%] (15 mmol Scale) | Amine Boiling Point [°C] | |
---|---|---|
NDIC3 | 35 | 47.8 |
NDIC4 | 51 | 78.0 |
NDIC5 | 88 | 104 |
NDIC6 | 82 | 131 |
NDIC7 | 75 | 155 |
NDIC8 | 85 | 176 |
NDIC9 | 78 | 200 |
NDIC10 | 79 | 217 |
NDIC11 | 68 | 242 |
Crystal System | Space Group | a | B | C | α | β | γ | dπ-π [Å] | |
---|---|---|---|---|---|---|---|---|---|
NDIC3 | orthorhombic | Pbca | 6.96 | 17.24 | 27.58 | 90.0 | 90.0 | 90.0 | n/a |
(7.15) | (17.49) | (27.80) | (90.0) | (90.0) | (90.0) | ||||
NDIC4 | triclinic | P | 5.22 | 7.84 | 11.13 | 103.7 | 94.3 | 93.9 | 3.34 |
(5.32) | (8.17) | (11.04) | (105.1) | (93.4) | (92.9) | ||||
NDIC5 | monoclinic | P21/c | 5.03 | 8.11 | 24.21 | 90.0 | 90.8 | 90.0 | 3.22 |
(5.12) | (7.94) | (26.24) | (90.0) | (91.6) | (90.0) | ||||
NDIC6 | triclinic | P | 4.90 | 8.28 | 14.52 | 96.3 | 98.1 | 93.6 | 3.32 |
(4.91) | (8.38) | (14.55) | (96.0) | (99.1) | (93.1) | ||||
NDIC7 | monoclinic | P21/c | 7.87 | 4.84 | 33.02 | 90.0 | 92.0 | 90.0 | 3.27 |
(-) | (-) | (-) | (-) | (-) | (-) | ||||
NDIC8 | triclinic | P | 4.77 | 6.53 | 22.71 | 87.9 | 88.9 | 75.8 | 3.36 |
(4.86) | (6.63) | (22.87) | (88.7) | (89.9) | (75.3) | ||||
NDIC9 | monoclinic | P21/c | 7.85 | 4.84 | 37.74 | 90.0 | 95.0 | 90.0 | 3.17 |
(7.95) | (4.91) | (38.06) | (90.0) | (94.9) | (90.0) | ||||
NDIC10 | triclinic | P | 4.73 | 6.55 | 25.58 | 94.2 | 95.3 | 104.3 | 3.31 |
(4.81) | (6.70) | (26.09) | (93.2) | (95.8) | (105.2) | ||||
NDIC11 | monoclinic | P21/c | 7.85 | 4.87 | 42.51 | 90.0 | 92.1 | 90.0 | 3.14 |
(-) | (-) | (-) | (-) | (-) | (-) |
Electron Mobility—μe/10−4 × cm2V−1s−1 | Threshold Voltage—Vth/V | |
---|---|---|
NDIC3 | 0.16 ± 0.03 | 41 ± 3 |
NDIC4 | 0.55 ± 0.13 | 34 ± 2 |
NDIC5 | 0.12 ± 0.01 | 46 ± 1 |
NDIC6 | 1.55 ± 0.31 | 37 ± 1 |
NDIC7 | 2.49 ± 0.79 | 47 ± 6 |
NDIC8 | 1.24 ± 0.46 | 47 ± 3 |
NDIC9 | 0.15 ± 0.03 | 46 ± 3 |
NDIC10 | 0.08 ± 0.01 | 54 ± 3 |
NDIC11 | 0.56 ± 0.05 | 46 ± 2 |
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Chlebosz, D.; Goldeman, W.; Janus, K.; Szuster, M.; Kiersnowski, A. Synthesis, Solution, and Solid State Properties of Homological Dialkylated Naphthalene Diimides—A Systematic Review of Molecules for Next-Generation Organic Electronics. Molecules 2023, 28, 2940. https://doi.org/10.3390/molecules28072940
Chlebosz D, Goldeman W, Janus K, Szuster M, Kiersnowski A. Synthesis, Solution, and Solid State Properties of Homological Dialkylated Naphthalene Diimides—A Systematic Review of Molecules for Next-Generation Organic Electronics. Molecules. 2023; 28(7):2940. https://doi.org/10.3390/molecules28072940
Chicago/Turabian StyleChlebosz, Dorota, Waldemar Goldeman, Krzysztof Janus, Michał Szuster, and Adam Kiersnowski. 2023. "Synthesis, Solution, and Solid State Properties of Homological Dialkylated Naphthalene Diimides—A Systematic Review of Molecules for Next-Generation Organic Electronics" Molecules 28, no. 7: 2940. https://doi.org/10.3390/molecules28072940