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Bright Luminescence by Combining Chiral [2.2]Paracyclophane with a Boron-Nitrogen-Doped Polyaromatic Hydrocarbon Building Block.

ABSTRACT: Novel BN-doped compounds based on chiral, tetrasubstituted [2.2]paracyclophane and NBN-benzo[f,g]tetracene were synthesized by Sonogashira-Hagihara coupling. Conjugated ethynyl linkers allow electronic communication between the π-electron systems through-bond, whereas through-space interactions are provided by strong π-π overlap between the pairs of NBN-building blocks. Excellent optical and chiroptical properties in racemic and enantiopure conditions were measured, with molar absorption coefficients up to ϵ=2.04×105  M-1  cm-1 , fluorescence quantum yields up to ΦPL =0.70, and intense, mirror-image electronic circular dichroism and circularly polarized luminescence signals of the magnitude of 10-3 for the absorption and luminescence dissymmetry factors. Computed glum,calcd. values match the experimental ones. Electroanalytical data show both oxidation and reduction of the ethynyl-linked tetra-NBN-substituted paracyclophane, with an overlap of two redox processes for oxidation leading to a diradical dication.

SUBMITTER: Rapp MR 

PROVIDER: S-EPMC9306876 | biostudies-literature | 2022 Feb

REPOSITORIES: biostudies-literature

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Bright Luminescence by Combining Chiral [2.2]Paracyclophane with a Boron-Nitrogen-Doped Polyaromatic Hydrocarbon Building Block.

Rapp Mario R MR   Leis Wolfgang W   Zinna Francesco F   Di Bari Lorenzo L   Arnold Tamara T   Speiser Bernd B   Seitz Michael M   Bettinger Holger F HF  

Chemistry (Weinheim an der Bergstrasse, Germany) 20220120 11

Novel BN-doped compounds based on chiral, tetrasubstituted [2.2]paracyclophane and NBN-benzo[f,g]tetracene were synthesized by Sonogashira-Hagihara coupling. Conjugated ethynyl linkers allow electronic communication between the π-electron systems through-bond, whereas through-space interactions are provided by strong π-π overlap between the pairs of NBN-building blocks. Excellent optical and chiroptical properties in racemic and enantiopure conditions were measured, with molar absorption coeffic  ...[more]

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