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Simple aryl halides do not react with nucleophiles. However, nucleophilic aromatic substitutions can be forced under certain conditions, such as high temperatures or strong bases. The mechanism of substitution under such conditions involves the highly unstable and reactive benzyne intermediate. Benzyne contains equivalent carbon centers at both ends of the triple bond, each of which is equally susceptible to nucleophilic attack. This 50–50 distribution of products is...
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Fluorescent Carbazole-Derived Aza[5]Helicenes: Synthesis, Functionalization, and Characterization.

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Novel azahelicenes, including indolo[2,3-c]carbazole and cinnolino[3,4-c]carbazole, were synthesized and show promising fluorescence and aggregation-induced emission properties. These new helical compounds offer potential for advanced materials applications.

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aggregation‐induced emissionazaarenescross couplingfluorescencehelicenes

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Area of Science:

  • Organic Chemistry
  • Materials Science
  • Supramolecular Chemistry

Background:

  • Azahelicenes are a class of helical organic molecules with unique photophysical properties.
  • Developing new synthetic routes to functionalized azahelicenes is crucial for exploring their potential applications.

Purpose of the Study:

  • To synthesize novel indolo[2,3-c]carbazole (ICz), 9H-cinnolino[3,4-c]carbazole (CnCz), and indolo[2,3-k]- and -[3,2-a]phenanthridine (IP) derivatives.
  • To investigate the photophysical properties, including fluorescence, acidochromism, and aggregation-induced emission (AIE) of the synthesized compounds.
  • To elucidate the helical structure and electronic properties using experimental and computational methods.

Main Methods:

  • Ortho fusion strategy employing Suzuki cross couplings, intramolecular nitrene insertions, diazo couplings, and Morgan-Walls cyclizations.
  • Transformation of IPs into organoboranes and helicene conjugates with tetraphenylethylene derivatives.
  • X-ray crystallographic analysis and quantum chemical calculations for structural and electronic characterization.

Main Results:

  • Successful synthesis of ICz, CnCz, and various substituted IPs.
  • Compounds exhibit fluorescence with large Stokes shifts, strong acidochromism, and good to excellent AIE.
  • Helical structures confirmed; HOMO-LUMO gaps of 3.96-4.06 eV calculated.
  • CnCz displays a small singlet-triplet inversion; relative pKa values range from 6.65-9.55.

Conclusions:

  • The developed ortho fusion strategy provides access to a diverse range of functionalized azahelicenes.
  • The synthesized azahelicenes possess desirable photophysical properties for potential applications in optoelectronics and sensing.
  • Further studies on structure-property relationships can guide the design of advanced helical materials.