Richter M, Hahn S, Dmitrieva E, Rominger F, Popov A, Bunz UHF, Feng X, Berger R (2019)
Publication Type: Journal article
Publication year: 2019
Book Volume: 25
Pages Range: 1345-1352
Journal Issue: 5
Polycyclic aromatic azomethine ylides (PAMYs) are powerful building blocks in the bottom-up synthesis of internally nitrogen-containing polycyclic aromatic hydrocarbons (N-PAHs) through 1,3-cycloaddition reactions. In this work, the cycloaddition reaction of PAMYs to asymmetric ortho-quinones is presented, which, in contrast to the addition to symmetric para-quinones, facilitates subsequent condensation reactions and allows the synthesis of three helical N-PAHs with ullazine-quinoxaline (UQ-1–3) backbones. UQ-1 and UQ-2 possess two helical centers; however, single-crystal X-ray analysis together with the computational modeling of UQ-3 elucidate the formation of only the thermodynamically most stable geometry with four helical centers in a (P,P,M,M) configuration. For the series UQ-1–3, the number of redox steps is directly correlated with the number of ullazine or quinoxaline units incorporated into the targeted molecular backbones. A detailed investigation of the spectroscopic and magnetic properties of the radical cation and anion as well as the dication and dianion species by in situ EPR/UV/Vis-NIR spectroelectrochemistry is provided. The excellent optical and redox properties combined with helical geometries render them possibly applicable as chiral emitter or ambipolar charge transport material in organic electronics.
APA:
Richter, M., Hahn, S., Dmitrieva, E., Rominger, F., Popov, A., Bunz, U.H.F.,... Berger, R. (2019). Helical Ullazine-Quinoxaline-Based Polycyclic Aromatic Hydrocarbons. Chemistry - A European Journal, 25(5), 1345-1352. https://doi.org/10.1002/chem.201804751
MLA:
Richter, Marcus, et al. "Helical Ullazine-Quinoxaline-Based Polycyclic Aromatic Hydrocarbons." Chemistry - A European Journal 25.5 (2019): 1345-1352.
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