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Related Concept Videos

¹H NMR of Conformationally Flexible Molecules: Temporal Resolution00:52

¹H NMR of Conformationally Flexible Molecules: Temporal Resolution

At room temperature, the chair conformer of cyclohexane undergoes rapid ring flipping between two equivalent chair conformers at a rate of approximately 105 times per second. These two chair conformers are in equilibrium. The rapid ring flipping results in the interconversion of the axial proton to an equatorial proton and an equatorial to the axial proton. Such interconversions are too rapid and cannot be detected on the NMR timescale. Hence, the NMR spectrometer cannot distinguish between the...
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Replacing each alpha-hydrogen in chloroethane by bromine (or a different functional group) yields a pair of enantiomers. Such protons are called prochiral or enantiotopic and are related by a mirror plane. Enantiotopic protons are chemically equivalent in an achiral environment. Because most proton NMR spectra are recorded using achiral solvents, enantiotopic hydrogens yield a single signal.
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Chirality is most prevalent in carbon-based tetrahedral compounds, but this important facet of molecular symmetry extends to sp3-hybridized nitrogen, phosphorus and sulfur centers, including trivalent molecules with lone pairs. Here, the lone pair behaves as a functional group in addition to the other three substituents to form an analogous tetrahedral center that can be chiral.
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Related Experiment Video

Updated: Jul 12, 2026

High-Contrast and Fast Photorheological Switching of a Twist-Bend Nematic Liquid Crystal
06:24

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Published on: October 31, 2019

Tunable Synthesis of Multi-Responsive NH-Containing Helical Nanographenes With a Chiroptical Switching Function.

Chihiro Maeda1,2, Sayaka Michishita1, Issa Yasutomo1

  • 1Graduate School of Environmental, Life, Natural Science and Technology, Okayama University, Tsushima, Okayama, Japan.

Angewandte Chemie (International Ed. in English)
|July 10, 2026
PubMed
Summary

We developed a new method to synthesize helical nanographenes (HNGs) using carbazole frameworks. These HNGs exhibit tunable chiroptical properties and pH-responsive circularly polarized luminescence (CPL).

Keywords:
chiralitycircularly polarized luminescencehelical nanographenesion sensingproton transfer

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Last Updated: Jul 12, 2026

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Published on: March 4, 2021

Area of Science:

  • Organic Chemistry
  • Materials Science
  • Supramolecular Chemistry

Background:

  • Helical nanographenes (HNGs) are known for their red-region chiroptical properties.
  • Current synthesis methods, often using hexa-peri-hexabenzocoronene (HBC) via Diels-Alder and Scholl reactions, require harsh conditions (>200°C), limiting structural diversity and modular tuning.

Purpose of the Study:

  • To report a tunable synthesis of NH-containing HNGs based on carbazole frameworks.
  • To enable π-extension without protecting the NH group.
  • To explore the chiroptical properties and pH-responsive switching of these novel HNGs.

Main Methods:

  • Multifold Scholl reactions of 1,3,6,8-tetrakis(oligophenyl)-appended carbazoles derived from a common 1,3,6,8-tetrabromocarbazole platform.
  • Uniform installation of arene units for π-extension, forming up to 12 C─C bonds.
  • Resolution of enantiopure forms using chiral High-Performance Liquid Chromatography (HPLC).

Main Results:

  • Successfully synthesized NH-containing HNGs with tunable structures.
  • Formation of up to 12 C─C bonds at defined positions, suppressing regioisomer formation due to identical arenes and symmetric framework.
  • Resolved HNGs exhibited distinct chiroptical properties, including a pronounced redshift and reversible on/off switching of circularly polarized luminescence (CPL) upon pH change.
  • Excited-state proton transfer generated anionic species with redshifted fluorescence and CPL under neutral conditions.

Conclusions:

  • Developed a modular and tunable synthesis for NH-containing helical nanographenes (HNGs) using carbazole frameworks.
  • Demonstrated pH-driven chiroptical switching of CPL in HNGs due to unprotected NH groups.
  • Highlighted the potential of these HNGs for applications requiring responsive chiroptical materials.