Boosting quantum yields and circularly polarized luminescence of penta- and hexahelicenes by doping with two BN-groups

Yannik Appiarius; Sandra Míguez-Lago; Pim Puylaert; Noah Wolf; Sourabh Kumar; Martin Molkenthin; Delia Miguel; Tim Neudecker; Michal Juríček; Araceli G. Campaña; Anne Staubitz

doi:10.1039/D3SC02685J

Boosting quantum yields and circularly polarized luminescence of penta- and hexahelicenes by doping with two BN-groups†

Yannik Appiarius,

^ab Sandra Míguez-Lago,

^c Pim Puylaert,

^d Noah Wolf,

^a Sourabh Kumar,

^e Martin Molkenthin,^a Delia Miguel,

^f Tim Neudecker,

^beg Michal Juríček,

^h Araceli G. Campaña

^c and Anne Staubitz

*^ab

Author affiliations

* Corresponding authors

^a University of Bremen, Institute for Organic and Analytical Chemistry, 28359 Bremen, Germany
E-mail: staubitz@uni-bremen.de

^b University of Bremen, MAPEX Center for Materials and Processes, 28359 Bremen, Germany

^c University of Granada, Department of Organic Chemistry, Unidad de Excelencia de Química, 18071 Granada, Spain

^d University of Bremen, Institute for Inorganic Chemistry and Crystallography, 28359 Bremen, Germany

^e University of Bremen, Institute for Physical and Theoretical Chemistry, 28359 Bremen, Germany

^f University of Granada, Department of Physical Chemistry, Unidad de Excelencia de Química, 18071 Granada, Spain

^g University of Bremen, Bremen Center for Computational Materials Science, 28359 Bremen, Germany

^h University of Zurich, Department of Chemistry, 8057 Zurich, Switzerland

Abstract

The incorporation of boron–nitrogen (BN) units into polycyclic aromatic hydrocarbons (PAHs) as an isoelectronic replacement of two carbon atoms can significantly improve their optical properties, while the geometries are mostly retained. We report the first non-π-extended penta- and hexahelicenes comprising two aromatic 1,2-azaborinine rings. Comparing them with their all-carbon analogs regarding structural, spectral and (chir)optical properties allowed us to quantify the impact of the heteroatoms. In particular, BN-hexahelicene BN[6] exhibited a crystal structure congruent with its analog CC[6], but displayed a fivefold higher fluorescence quantum yield (φ_fl = 0.17) and an outstanding luminescence dissymmetry factor (|g_lum| = 1.33 × 10⁻²). Such an unusual magnification of both properties at the same time makes BN-helicenes suitable candidates as circularly polarized luminescence emitters for applications in materials science.

This article is part of the themed collection: 2024 Chemical Science Covers

Chemical Science

Boosting quantum yields and circularly polarized luminescence of penta- and hexahelicenes by doping with two BN-groups†

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Boosting quantum yields and circularly polarized luminescence of penta- and hexahelicenes by doping with two BN-groups

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