Synthesis of Ethano-Bridged Diazapolycenes as Potential Precursors for Diazapolycenes and Their Properties
Abstract
:1. Introduction
2. Results and Discussions
2.1. Synthesis
2.2. Attempts to Convert 7 to the Corresponding Diazapolycenes 8
2.3. Spectroscopic Properties
2.4. Structural and Thermal Properties
3. Experimental Section
3.1. General Information
3.2. Synthesis and Characterization of the Products
6,13-Dihydro-6,13-ethano-5,12-diazapentacene (7a)
7,16-Dihydro-7,16-ethanobenzo[b]benzo[6,7]quinolino[3,2-i]acridine (7,16-dihydro-7,16-ethano-6,15-diaza-heptacene, 7b)
8,19-Dihydro-8,19-ethanonaphtho[2,3-b]naphtho[2′,3′:6,7]quinolino[3,2-i]acridine (8,19-dihydro-8,19-ethano-7,18-diazanonacene, 7c)
3.3. Attempted Synthesis of Diazapolycenes 8
3.4. Measurement of Quantum Yield (Φ)
4. Conclusions
Acknowledgments
Author Contributions
Conflicts of Interest
References
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Compounds | H4 | H at Peri-Position | -CH2CH2- |
---|---|---|---|
Quinoline (a) | 8.00 (3J = 8.3, 4J = 1.1 Hz) | 8.05 (3J = 8.2, 4J = 1.6 Hz) | |
Benzo[g]quinoline | 8.58 (3J = 8.5, 4J = 1 Hz) (b) 8.31 (3J = 8.5 Hz) (c) | 8.76 (s) (b) 8.70 (s) (c) | |
Naphtho[2,3-g]quinoline (d) | 8.50 (3J = 7.5, 4J = 1.5 Hz) | 8.87 (s) | |
5-Azapentacene (e) | 9.12 (s) | 9.26 (s) | |
7a | 7.60 (s) | 8.01 (3J = 8.3, 4J = 1.2 Hz) | 2.03 (s) |
7b | 8.33 (s) | 8.59 (s) | 2.25–2.10 (m) |
7c | 8.73 (s) | 8.85 (s) | 2.27–2.23 (m) |
Compd. | λ [nm (logε)] | λexcit | λemit | Quantum Yield (a) |
---|---|---|---|---|
7a | 245 (5.49) 331 (5.18) | 245 | 400 | 0.38 |
7b | 256 (5.20, sh) 280 (5.46) 297 (5.20, sh) 350 (4.61) 370 (4.81) | 280 | 465 | 0.54 |
7c | 257 (5.39) 303 (5.46) 325 (5.41) 408 (4.85) | 303 | 500 | 0.58 |
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Karim, M.; Jahng, Y. Synthesis of Ethano-Bridged Diazapolycenes as Potential Precursors for Diazapolycenes and Their Properties. Molecules 2016, 21, 407. https://doi.org/10.3390/molecules21040407
Karim M, Jahng Y. Synthesis of Ethano-Bridged Diazapolycenes as Potential Precursors for Diazapolycenes and Their Properties. Molecules. 2016; 21(4):407. https://doi.org/10.3390/molecules21040407
Chicago/Turabian StyleKarim, Moinul, and Yurngdong Jahng. 2016. "Synthesis of Ethano-Bridged Diazapolycenes as Potential Precursors for Diazapolycenes and Their Properties" Molecules 21, no. 4: 407. https://doi.org/10.3390/molecules21040407