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Synthesis and Properties of Dibenzo-Fused Naphtho[2,3-b:6,7-b′]disilole and Naphtho[2,3-b:6,7-b′]diphosphole

Authors :
Suzuho Morishita
Chikara Hayasaka
Keiichi Noguchi
Koji Nakano
Source :
Molecules, Vol 29, Iss 18, p 4313 (2024)
Publication Year :
2024
Publisher :
MDPI AG, 2024.

Abstract

Silole- and phosphole-containing polycyclic aromatic compounds have attracted significant attention in the field of organic functional materials. The structure of the aromatic units has great impact on the photophysical properties of the resulting silole- and phosphole-containing polycyclic aromatic compounds. Here, dibenzo-fused naphtho[2,3-b:6,7-b′]disilole (NDS) and naphtho[2,3-b:6,7-b′]diphosphole (NDP), where a naphthalene unit is arranged between two silole and phosphole units, respectively, were designed and synthesized. The solid-state structures of them were confirmed by X-ray crystallographic analysis. The photophysical properties were evaluated by UV−vis absorption and photoluminescence spectroscopies and compared with those of their related compounds, such as dibenzo-fused silolo[3,2-b]silole and benzo[1,2-b:4,5-b′]disilole, ever reported. The longest wavelength absorption band of a series of silole-fused compounds was found to be red-shifted in the order benzo[1,2-b:4,5-b′]disilole < NDS < silolo[3,2-b]silole derivatives. For a series of phosphole-fused compounds, π-extension from phospholo[3,2-b]phosphole to NDP derivatives induces the lower absorption coefficient of the longest wavelength absorption band and the red-shift of the second longest wavelength absorption band. Both NDS and NDP exhibit much lower fluorescence quantum yields than their related compounds.

Details

Language :
English
ISSN :
14203049
Volume :
29
Issue :
18
Database :
Directory of Open Access Journals
Journal :
Molecules
Publication Type :
Academic Journal
Accession number :
edsdoj.b55225f2f7443ce9bfad4b1148a89eb
Document Type :
article
Full Text :
https://doi.org/10.3390/molecules29184313