1,6- and 1,7-Regioisomers of Highly Soluble Amino-Substituted Perylene Tetracarboxylic Dianhydrides: Synthesis, Optical and Electrochemical Properties
Abstract
:1. Introduction
2. Experimental Section
2.1. General
2.2. Synthesis
2.2.1. Synthesis of 1,7- and 1,6-Dinitroperylene Diimides (7 and 8)
2.2.2. Synthesis of 1,7- and 1,6-Diaminoperylene Diimides (5 and 6)
2.2.3. General Procedure for Alkylation (3a–3c and 4a–4c)
2.2.4. General Procedure for Saponification (1a–1c and 2a–2c)
3. Results and Discussion
3.1. Synthesis
3.2. Optical Properties
1a/1b/1c | λabs (nm) a | log ε b | λem (nm) a | Stokes shift (nm) | Φ c × 102 |
---|---|---|---|---|---|
cyclohexane | 678/679/679 | 4.67/4.66/4.64 | 717/716/716 | 39/37/37 | 4.31/3.71/3.32 |
diethyl ether | 683/686/686 | 4.67/4.66/4.64 | 732/733/732 | 49/47/46 | 0.52/0.51/0.62 |
ethyl acetate | 698/698/699 | 4.67/4.66/4.64 | 753/753/755 | 55/55/56 | 0.14/0.13/0.12 |
dichloromethane | 713/714/714 | 4.68/4.67/4.65 | 775/771/773 | 59/57/58 | 0.13/0.24/0.26 |
acetonitrile | 714/714/713 | 4.66/4.66/4.64 | 794/792/791 | 80/78/78 | 0.11/0.15/0.16 |
2a/2b/2c | λabs (nm) a | ε b (M−1·cm−1) | λem (nm) a | Stokes shift (nm) | Φ c × 103 |
---|---|---|---|---|---|
cyclohexane | 632/632/633 | 4.69/4.69/4.68 | 721/721/719 | 89/89/86 | 2.28/2.87/2.86 |
diethyl ether | 634/639/641 | 4.69/4.69/4.68 | 735/736/732 | 101/97/91 | 0.48/0.38/0.65 |
ethyl acetate | 652/649/653 | 4.69/4.68/4.68 | 760/755/757 | 108/106/101 | 0.27/0.32/0.40 |
dichloromethane | 672/671/674 | 4.70/4.69/4.67 | 791/787/792 | 119/116/118 | 0.20/0.18/0.23 |
acetonitrile | 667/671/670 | 4.69/4.68/4.67 | 800/799/799 | 133/128/129 | 0.15/0.17/0.19 |
3.3. Quantum Chemistry Computation
Compound | HOMO a | LUMO a | Eg a | Eg b | Twisting angle (°) a |
---|---|---|---|---|---|
1a | −5.63 | −3.52 | 2.11 | 1.83 | 17.21, 17.30 |
1b | −5.62 | −3.52 | 2.10 | 1.83 | 17.23, 17.33 |
1c | −5.62 | −3.52 | 2.10 | 1.83 | 17.26, 17.35 |
2a | −5.70 | −3.51 | 2.19 | 1.96 | 19.36, 19.56 |
2b | −5.70 | −3.51 | 2.19 | 1.96 | 19.38, 19.59 |
2c | −5.69 | −3.51 | 2.18 | 1.96 | 19.41, 19.61 |
3.4. Electrochemical Properties
Compound | E+1/2 a | E-1/2 a | E2-1/2 a | HOMO b | LUMO b |
---|---|---|---|---|---|
1a | 0.95 | −0.80 | −1.02 | −5.56 | −3.73 |
1b | 0.94 | −0.81 | −1.03 | −5.55 | −3.72 |
1c | 0.93 | −0.83 | −1.03 | −5.54 | −3.71 |
2a | 1.03 | −0.81 | −1.01 | −5.64 | −3.68 |
2b | 1.02 | −0.82 | −1.02 | −5.63 | −3.67 |
2c | 1.02 | −0.83 | −1.03 | −5.63 | −3.67 |
3.5. Stacking Behaviors of Dyes in Solution and Solid State
4. Conclusions
Supplementary Materials
Acknowledgments
Author Contributions
Conflicts of Interest
References
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Chen, K.-Y.; Chang, C.-W.; Tsai, H.-Y. 1,6- and 1,7-Regioisomers of Highly Soluble Amino-Substituted Perylene Tetracarboxylic Dianhydrides: Synthesis, Optical and Electrochemical Properties. Materials 2015, 8, 4943-4960. https://doi.org/10.3390/ma8084943
Chen K-Y, Chang C-W, Tsai H-Y. 1,6- and 1,7-Regioisomers of Highly Soluble Amino-Substituted Perylene Tetracarboxylic Dianhydrides: Synthesis, Optical and Electrochemical Properties. Materials. 2015; 8(8):4943-4960. https://doi.org/10.3390/ma8084943
Chicago/Turabian StyleChen, Kew-Yu, Che-Wei Chang, and Hsing-Yang Tsai. 2015. "1,6- and 1,7-Regioisomers of Highly Soluble Amino-Substituted Perylene Tetracarboxylic Dianhydrides: Synthesis, Optical and Electrochemical Properties" Materials 8, no. 8: 4943-4960. https://doi.org/10.3390/ma8084943