Beilstein J. Org. Chem.2025,21, 270–276, doi:10.3762/bjoc.21.19
-0495, Japan X-ray diffraction facility, Department of Chemistry, 100 E. 24th Street, The University of Texas at Austin, Austin, TX 78712, USA 10.3762/bjoc.21.19 Abstract A benzo[rst]pentaphene (BPP) substituted by an isopropoxy group (BPP-OiPr) was synthesized in a facile manner. Its photophysical
properties were investigated by UV–vis absorption and fluorescence spectroscopy in compassion to pristine BPP and its oxidation product, benzo[rst]pentaphene-5,8-dione (BPP-dione). BPP-OiPr exhibited a significantly enhanced photoluminescence quantum yield (PLQY), reaching 73% in comparison to pristine BPP
by scanning electron microscopy. The intriguing optical properties of BPP and its derivatives may lead to their application as fluorophores.
Keywords: benzo[rst]pentaphene; intramolecular charge transfer; nanocrystals; photoluminescence; polycyclic aromatic hydrocarbon; Introduction
Polycyclic
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Graphical Abstract
Scheme 1:
Synthesis of BPP-OiPr 3 and BPP-dione 4.
Beilstein J. Org. Chem.2024,20, 2921–2930, doi:10.3762/bjoc.20.244
modification of dihydroxyviolanthrone where the effect of three alkoxy substituents on the 16,17-bis(2-ethylhexyloxy)anthra[9,1,2-cde]benzo[rst]pentaphene-5,10-dione, on aggregation and photovoltaic properties was studied [30]. It was found that derivatives with the shortest linear alkyl chain (n-hexyl
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Graphical Abstract
Figure 1:
Chemical structures of violanthrone and dihydroxyviolanthrone.