Optically pure, monodisperse cis-oligodiacetylenes: Aggregation-induced chirality enhancement

Chernick E, Börzsönyi G, Steiner C, Ammon MM, Geßner D, Frühbeißer S, Gröhn F, Maier S, Tykwinski R (2014)

Publication Type: Journal article, Original article

Publication year: 2014


Original Authors: Chernick E.T., Börzsönyi G., Steiner C., Ammon M., Gessner D., Frühbeißer S., Gröhn F., Maier S., Tykwinski R.R.

Publisher: Wiley-VCH Verlag

Book Volume: 53

Pages Range: 310-314

Journal Issue: 1

DOI: 10.1002/anie.201307904


Conformational changes in the conjugated backbone of poly- and oligodiacetylenes (PDAs and ODAs) play an important role in determining the electronic properties of these compounds. At the same time, conformational changes can also result in a folded structure that shows helical chirality. Using D-camphor as a chiral building block, we have designed a high-yielding, iterative synthesis of monodisperse, optically pure cis-oligodiacetylenes (ODAs). cis-ODAs up to the tridecamer have been formed, which is the longest monodisperse cis-ODA reported to date. UV/Vis spectroscopy suggests a large effective conjugation length in THF, likely the result of a linear, planar conformation in this solvent. High-resolution STM/AFM measurements of the nonamer cast from THF onto HOPG show a linear structure. In iPrOH, circular dichroism (CD) spectra suggest the formation of chiral aggregates for ODAs with at least nine D-camphor units, based on a strong CD response. Conformation, conjugation: A series of optically pure, monodisperse cis-oligodiacetylenes (cis-ODAs) based on D-camphor building blocks has been synthesized up to the tridecamer length, which represents the longest cis-ODA reported to date. Optical spectroscopy and STM/AFM measurements indicate that the oligomers assume a linear, planar conformation in THF. Conversely, in iPrOH solution ODAs with n≥9 form chiral aggregates. Copyright © 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

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Chernick, E., Börzsönyi, G., Steiner, C., Ammon, M.M., Geßner, D., Frühbeißer, S.,... Tykwinski, R. (2014). Optically pure, monodisperse cis-oligodiacetylenes: Aggregation-induced chirality enhancement. Angewandte Chemie International Edition, 53(1), 310-314. https://doi.org/10.1002/anie.201307904


Chernick, Erin, et al. "Optically pure, monodisperse cis-oligodiacetylenes: Aggregation-induced chirality enhancement." Angewandte Chemie International Edition 53.1 (2014): 310-314.

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