Abstract
Phosphole-fused π-conjugated acenes have been attracting interest because of the attractive features of the phosphole moiety, such as fluorescence and chemically modifiable properties. Herein, 6-phenyl-6H-benzo[f]naphtho[2,3-b]phosphoindole was prepared by reacting dichlorophenylphosphine with a dilithium intermediate derived from 3,3′-dibromo-2,2′-binaphthyl. Various derivatives, such as a phospholium salt and a borane–phosphole complex with functional groups on the phosphorus atom were synthesized using the obtained phosphole as a common starting material. Single-crystal X-ray analysis of the parent benzo[f]naphtho[2,3-b]phosphoindole revealed that the pentacyclic ring is almost planar. Fluorescence spectroscopy data showed that the phosphole derivatives, such as phosphine oxide and the phospholium salt and borane complex exhibited photoluminescence in chloroform.
Highlights
Phosphole-based heteroacenes are attracting increasing interest in various fields, such as organic synthesis, structural chemistry, and materials science [1,2,3,4]
This paper presents the synthesis, molecular structure, and optical properties of 6-phenyl-6Hbenzo[f]naphtho[2,3-b]phosphoindole (F) and the derivatives in which the phosphorus atom is chemically modified, such as a phospholium salt and the borane–phosphine complex
The obtained product was used as a key compound for the chemical modification of the phosphorus atom
Summary
Phosphole-based heteroacenes are attracting increasing interest in various fields, such as organic synthesis, structural chemistry, and materials science [1,2,3,4]. This paper presents the synthesis, molecular structure, and optical properties of 6-phenyl-6Hbenzo[f]naphtho[2,3-b]phosphoindole (F) and the derivatives in which the phosphorus atom is chemically modified, such as a phospholium salt and the borane–phosphine complex. These results show that all phosphole derivatives had a symmetric structure in solution.
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