Pyrene-Fused s-Indacene
Melidonie J, Liu J, Fu Y, Weigand JJ, Berger R, Feng X (2018)
Publication Type: Journal article
Publication year: 2018
Journal
Book Volume: 83
Pages Range: 6633-6639
Journal Issue: 12
Abstract
One antiaromatic polycyclic hydrocarbon (PH) with and without solubilizing tert-butyl substituents, namely s-indaceno[2,1-a:6,5-a′]dipyrene (IDPs), has been synthesized by a four-step protocol. The IDPs represent the longitudinal, peri-extension of the indeno[1,2-b]fluorene skeleton towards a planar 40 π-electron system. Their structures were unambiguously confirmed by X-ray crystallographic analysis. The optoelectronic properties were studied by UV/vis absorption spectroscopy and cyclic voltammetry. These studies revealed that peri-fusion renders the IDP derivatives with a narrow optical energy gap of 1.8 eV. The maximum absorption of IDPs is shifted by 160 nm compared to the parent indenofluorene. Two quasi-reversible oxidation as well as reduction steps indicate an excellent redox behavior attributed to the antiaromatic core. Formation of the radical cation and the dication was monitored by UV/vis absorption spectroscopy during titration experiments. Notably, the fusion of s-indacene with two pyrene moieties lead to IDPs with absorption maxima approaching the near infrared (NIR) regime.
Involved external institutions
Germany (DE)How to cite
APA:
Melidonie, J., Liu, J., Fu, Y., Weigand, J.J., Berger, R., & Feng, X. (2018). Pyrene-Fused s-Indacene. Journal of Organic Chemistry, 83(12), 6633-6639. https://doi.org/10.1021/acs.joc.8b00925
MLA:
Melidonie, Jason, et al. "Pyrene-Fused s-Indacene." Journal of Organic Chemistry 83.12 (2018): 6633-6639.
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