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

Journal article
(Original article)

Publication Details

Author(s): Chernick E, Börzsönyi G, Steiner C, Ammon M, Geßner D, Frühbeißer S, Gröhn F, Maier S, Tykwinski R
Journal: Angewandte Chemie-International Edition
Publisher: Wiley-VCH Verlag
Publication year: 2014
Volume: 53
Journal issue: 1
Pages range: 310-314
ISSN: 1433-7851


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.

FAU Authors / FAU Editors

Ammon, Maximilian
Professur für Experimentalphysik (Rastersondenmikroskopie)
Chernick, Erin
Sonderforschungsbereich 953/2 Synthetische Kohlenstoffallotrope
Frühbeißer, Sabine
Interdisziplinäres Zentrum für Molekulare Materialien
Geßner, David
Sonderforschungsbereich 953/2 Synthetische Kohlenstoffallotrope
Gröhn, Franziska Prof. Dr.
Professur für Molekulare Nanostrukturen
Maier, Sabine Prof. Dr.
Professur für Experimentalphysik (Rastersondenmikroskopie)
Steiner, Christian
Sonderforschungsbereich 953/2 Synthetische Kohlenstoffallotrope
Tykwinski, Rik Prof.
Lehrstuhl für Organische Chemie I

Additional Organisation
Exzellenz-Cluster Engineering of Advanced Materials
Graduiertenkolleg 1896/2 In situ Mikroskopie mit Elektronen, Röntgenstrahlen und Rastersonden

Research Fields

B Nanoelectronic Materials
Exzellenz-Cluster Engineering of Advanced Materials
A2 Nanoanalysis and Microscopy
Exzellenz-Cluster Engineering of Advanced Materials

How to cite

Chernick, E., Börzsönyi, G., Steiner, C., Ammon, 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://dx.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.


Last updated on 2019-21-07 at 08:02