Boosting quantum yields and circularly polarized luminescence of penta- and hexahelicenes by doping with two BN-groups
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Royal Society of Chemistry
Appiarius, Y. et al. Boosting quantum yields and circularly polarized luminescence of penta- and hexahelicenes by doping with two BN-groups. Chem. Sci., 2023. [DOI: 10.1039/d3sc02685j]
SponsorshipMCIN/AEI/10.13039/501100011033: PID2021-127521NB-I00; European Regional Development Fund (ERDF); Ministerio de Economía y Competitividad (BES-2016-076371); Spanish Junta de Andalucía; European Research Council (ERC); European Union's Horizon 2020: 716139; Swiss National Science Foundation (SNSF: PP00P2_198900); University of Granada
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 exhibited a crystal structure congruent with its analog CC, but displayed a fivefold higher fluorescence quantum yield (φfl = 0.17) and an outstanding luminescence dissymmetry factor (|glum| = 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.