Abstract
Dibenzoperioctacene (DBPO) with extended zigzag edges was synthesized and unambiguously characterized by a combination of nuclear magnetic resonance (NMR), mass spectrometry, and single-crystal X-ray diffraction analysis. Variable-temperature (VT) NMR analysis indicated the closed-shell character of DBPO, yet an electron paramagnetic resonance (EPR) signal was observed at room temperature suggesting its potential open-shell diradicaloid nature. The bond lengths in the single-crystal structure of DBPO aligned more closely with those of open-shell teranthene than closed-shell bisanthene. Spin-unrestricted density functional theory (DFT) calculations using various methods supported that ground state of DBPO might be on the borderline between closed- and open-shell singlet states, with a large singlet-triplet energy gap (ΔEST), consistent with the VT-NMR and EPR results. UV-vis-near infrared (NIR) absorption spectrum showed the longest-wavelength peak at 905 nm, marking the NIR optical properties of DBPO. DBPO exhibited a tendency to react with atmospheric oxygen, which additionally hinted at its possible open-shell character. Furthermore, the oxidized species of non-fluorescent DBPO exhibited strong emission at 820 and 915 nm, which opens its potential for oxygen detection via a "turn-on" NIR fluorescence response.
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