Polyacetylenes as Enantiodifferentiating Alignment Media

Meyer, Nils‐Christopher; Krupp, Alexis; Schmidts, Volker; Thiele, Christina M.; Reggelin, Michael

doi:10.1002/anie.201201891

Cited by 93 publications

(86 citation statements)

References 83 publications

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“…This behavior is fully reversible and contrasts with our results with p2 (Fig. b) . Unfortunately, as far as we are aware, no temperature‐dependent CD spectra of other amino acid containing aryl polyacetylenes are described whereby a comparison with similar polymers would be possible.…”

Section: Synthesis and Characterization Of Polyacetylenescontrasting

confidence: 99%

“…As expected from the work of Yashima[25b] and our own experience with p2 , both polymers form lyotropic liquid crystalline (LLC) phases in chloroform. We started our investigations with two LLC‐phases of p1 , denoted p1‐3‐300 and p1‐5‐300 in the following .…”

Section: Orientational Properties Of Lyotropic Liquid Crystalline Phasupporting

confidence: 72%

“…Although not as different as with p2 at 300 K, the calculated GCB of 0.65 clearly demonstrates a much higher enantiomer differentiating capability than PBLG (GCB = 0.991) at least for the IPC‐enantiomers.…”

Section: Orientational Properties Of Lyotropic Liquid Crystalline Phamentioning

confidence: 72%

“…). To our delight, the lines from the analyte are as narrow as those in p2 , and the RDCs are in the favorable range of about −10 to +15 Hz. To quantify the orientational differences of the two enantiomers of IPC, we calculated the corresponding alignment tensors ( A ) using a SVD‐based method within a modified version of the program hotFCHT .…”

Section: Orientational Properties Of Lyotropic Liquid Crystalline Phamentioning

confidence: 80%

“…The complete absence of the isotropic signal demonstrated the formation of a purely anisotropic phase. The choice of isopinocampheol (IPC) as an analyte is based on the fact that this alcohol is available in both enantiomeric forms and on the existence of three other studies probing the enantiomer differentiating properties of chiral LLC phases with this compound [12e, 14, 23]. For both samples, residual dipolar one‐bond couplings ( 1 D CH ) were extracted from CLIP‐HSQC spectra using the relation 1 T CH = 1 J CH + 2• 1 D CH (Fig.…”

Section: Orientational Properties Of Lyotropic Liquid Crystalline Phamentioning

confidence: 99%

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Phenylalanine‐based polyarylacetylenes as enantiomer‐differentiating alignment media

Krupp

Reggelin

2012

Magnetic Reson in Chemistry

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Lyotropic liquid crystalline phases of a phenylalanine-based polyacetylene are introduced as new enantiodifferentiating alignment media. Based on the unusual temperature dependence of the quadrupolar splitting of the (2)H-signal of the solvent (CDCl(3)), three distinct states of the phase with different orientational properties can be identified. This offers the opportunity to measure multiple alignment data sets without changing the sample. Unexpectedly, the largest difference in the orientation of the enantiomers of isopinocampheol was found in the high temperature domain of the phase. This is even more astonishing because the helical structure of the polymer backbone seems to break down at temperatures above approximately 10 °C, leaving the stereogenic centers of the amino acid moieties in the repeating units as the only reason for the enantiodifferentiation.

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Section: Synthesis and Characterization Of Polyacetylenescontrasting

confidence: 99%

Section: Orientational Properties Of Lyotropic Liquid Crystalline Phasupporting

confidence: 72%

Section: Orientational Properties Of Lyotropic Liquid Crystalline Phamentioning

confidence: 72%

Section: Orientational Properties Of Lyotropic Liquid Crystalline Phamentioning

confidence: 80%

Section: Orientational Properties Of Lyotropic Liquid Crystalline Phamentioning

confidence: 99%

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