Synthesis and characterizations of highly luminescent 5-isopropoxybenzo[<i>rst</i>]pentaphene

A benzo[<i>rst</i>]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[<i>rst</i>]pentaphene-5,8-dione (BPP-dione). BPP-OiPr exhibited a significantly enhanced photoluminescence quantum yield (PLQY), reaching 73% in comparison to pristine BPP (13%). BPP-dione, when compared to the parent BPP, also displayed improved absorption and emission from the first excited singlet (S<sub>1</sub>) state with a PLQY of 62% and an intramolecular charge-transfer character. The rod-like nano- to microcrystals as well as longer wires of these BPPs were also revealed by scanning electron microscopy. The intriguing optical properties of BPP and its derivatives may lead to their application as fluorophores.

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Publication Details

Journal
Beilstein Journal of Organic Chemistry
Published
2025-02-04
DOI
https://doi.org/10.3762/bjoc.21.19
Primary Topic
Organic Electronics and Photovoltaics
Type
article
Field-Weighted Citation Impact
0.00

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article

Synthesis and characterizations of highly luminescent 5-isopropoxybenzo[rst]pentaphene

Islam S. Marae, Rengo Yoshioka, Ryota Kabe, Eugene Khaskin et al.
Beilstein Journal of Organic Chemistry
Organic Electronics and Photovoltaics
article

Synthesis and characterizations of highly luminescent 5-isopropoxybenzo[rst]pentaphene

Islam S. Marae, Rengo Yoshioka, Ryota Kabe, Eugene Khaskin, Serhii Vasylevskyi, Jingyun Tan, Akimitsu Narita, Xiushang Xu, Zakaria Ziadi
article en

Abstract

A benzo[<i>rst</i>]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[<i>rst</i>]pentaphene-5,8-dione (BPP-dione). BPP-OiPr exhibited a significantly enhanced photoluminescence quantum yield (PLQY), reaching 73% in comparison to pristine BPP (13%). BPP-dione, when compared to the parent BPP, also displayed improved absorption and emission from the first excited singlet (S<sub>1</sub>) state with a PLQY of 62% and an intramolecular charge-transfer character. The rod-like nano- to microcrystals as well as longer wires of these BPPs were also revealed by scanning electron microscopy. The intriguing optical properties of BPP and its derivatives may lead to their application as fluorophores.

Beilstein Journal of Organic ChemistryVol. 21
Okinawa Institute of Science and Technology Graduate University (JP), The University of Texas at Austin (US)
Deutsche Forschungsgemeinschaft, Okinawa Institute of Science and Technology Graduate University, Japan Society for the Promotion of Science
Openalex Percentile: Top 98%
Organic Electronics and Photovoltaics
DOIOpen Access PDFOpenAlex
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Synthesis and characterizations of highly luminescent 5-isopropoxybenzo[<i>rst</i>]pentaphene — Islam S. Marae, Rengo Yoshioka, et al. · Beilstein Journal of Organic Chemistry (2025) | TGRS Research Map | TGRS