Octagon-Embedded Carbohelicene as a Chiral Motif for Circularly Polarized Luminescence Emission of Saddle-Helix Nanographenes
Miguel A. Medel
Departamento de Química Orgánica, Unidad de Excelencia de Química (UEQ), Facultad de Ciencias, Universidad de Granada, 18071 Granada, Spain
Search for more papers by this authorDr. Rubén Tapia
Departamento de Química Orgánica, Unidad de Excelencia de Química (UEQ), Facultad de Ciencias, Universidad de Granada, 18071 Granada, Spain
Search for more papers by this authorDr. Victor Blanco
Departamento de Química Orgánica, Unidad de Excelencia de Química (UEQ), Facultad de Ciencias, Universidad de Granada, 18071 Granada, Spain
Search for more papers by this authorDr. Delia Miguel
Departamento de Fisicoquímica, Facultad de Farmacia, UEQ, Universidad de Granada, Granada, Spain
Search for more papers by this authorCorresponding Author
Dr. Sara P. Morcillo
Departamento de Química Orgánica, Unidad de Excelencia de Química (UEQ), Facultad de Ciencias, Universidad de Granada, 18071 Granada, Spain
Search for more papers by this authorCorresponding Author
Dr. Araceli G. Campaña
Departamento de Química Orgánica, Unidad de Excelencia de Química (UEQ), Facultad de Ciencias, Universidad de Granada, 18071 Granada, Spain
Search for more papers by this authorMiguel A. Medel
Departamento de Química Orgánica, Unidad de Excelencia de Química (UEQ), Facultad de Ciencias, Universidad de Granada, 18071 Granada, Spain
Search for more papers by this authorDr. Rubén Tapia
Departamento de Química Orgánica, Unidad de Excelencia de Química (UEQ), Facultad de Ciencias, Universidad de Granada, 18071 Granada, Spain
Search for more papers by this authorDr. Victor Blanco
Departamento de Química Orgánica, Unidad de Excelencia de Química (UEQ), Facultad de Ciencias, Universidad de Granada, 18071 Granada, Spain
Search for more papers by this authorDr. Delia Miguel
Departamento de Fisicoquímica, Facultad de Farmacia, UEQ, Universidad de Granada, Granada, Spain
Search for more papers by this authorCorresponding Author
Dr. Sara P. Morcillo
Departamento de Química Orgánica, Unidad de Excelencia de Química (UEQ), Facultad de Ciencias, Universidad de Granada, 18071 Granada, Spain
Search for more papers by this authorCorresponding Author
Dr. Araceli G. Campaña
Departamento de Química Orgánica, Unidad de Excelencia de Química (UEQ), Facultad de Ciencias, Universidad de Granada, 18071 Granada, Spain
Search for more papers by this authorAbstract
We report a new family of hexa-peri-hexabenzocoronene (HBC)-based helical nanographenes incorporating π-extended carbo[5]helicenes bearing an octagonal carbocycle. This family represents a new kind of highly distorted saddle-helix hybrid nanographenes. For the first time, the eight-membered ring becomes a constituent of both a carbo[5]helicene and a HBC and thus, the negative curvature is responsible for twisting both units. This novel chiral motif, namely, oct-[5]helicene results in the largest torsion angle recorded so far for a carbo[5]helicene (θ=79.5°), as it has been suggested by DFT-calculations and confirmed by X-ray crystallography. Consequently, the barriers of isomerization become exceptionally high for a [5]helicene unsubstituted in the fjord region since neither racemization nor decomposition were observed at 200 °C for 1 or 3 during 5 h. Therefore, racemic resolutions allowed subsequent chiroptical studies showing the ECD and CPL responses of this novel family of chiral nanographenes.
Conflict of interest
The authors declare no conflict of interest.
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