Cargando…
Synthesis, structural characterization, and optical properties of benzo[f]naphtho[2,3-b]phosphoindoles
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 dil...
Autores principales: | , , , , , , , |
---|---|
Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
Beilstein-Institut
2021
|
Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7940816/ https://www.ncbi.nlm.nih.gov/pubmed/33747236 http://dx.doi.org/10.3762/bjoc.17.56 |
_version_ | 1783662022200655872 |
---|---|
author | Matsumura, Mio Teramoto, Takahiro Kawakubo, Masato Kawahata, Masatoshi Murata, Yuki Yamaguchi, Kentaro Uchiyama, Masanobu Yasuike, Shuji |
author_facet | Matsumura, Mio Teramoto, Takahiro Kawakubo, Masato Kawahata, Masatoshi Murata, Yuki Yamaguchi, Kentaro Uchiyama, Masanobu Yasuike, Shuji |
author_sort | Matsumura, Mio |
collection | PubMed |
description | 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. |
format | Online Article Text |
id | pubmed-7940816 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2021 |
publisher | Beilstein-Institut |
record_format | MEDLINE/PubMed |
spelling | pubmed-79408162021-03-18 Synthesis, structural characterization, and optical properties of benzo[f]naphtho[2,3-b]phosphoindoles Matsumura, Mio Teramoto, Takahiro Kawakubo, Masato Kawahata, Masatoshi Murata, Yuki Yamaguchi, Kentaro Uchiyama, Masanobu Yasuike, Shuji Beilstein J Org Chem Letter 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. Beilstein-Institut 2021-03-05 /pmc/articles/PMC7940816/ /pubmed/33747236 http://dx.doi.org/10.3762/bjoc.17.56 Text en Copyright © 2021, Matsumura et al. https://creativecommons.org/licenses/by/4.0https://www.beilstein-journals.org/bjoc/terms/termsThis is an Open Access article under the terms of the Creative Commons Attribution License (https://creativecommons.org/licenses/by/4.0). Please note that the reuse, redistribution and reproduction in particular requires that the author(s) and source are credited and that individual graphics may be subject to special legal provisions. The license is subject to the Beilstein Journal of Organic Chemistry terms and conditions: (https://www.beilstein-journals.org/bjoc/terms/terms) |
spellingShingle | Letter Matsumura, Mio Teramoto, Takahiro Kawakubo, Masato Kawahata, Masatoshi Murata, Yuki Yamaguchi, Kentaro Uchiyama, Masanobu Yasuike, Shuji Synthesis, structural characterization, and optical properties of benzo[f]naphtho[2,3-b]phosphoindoles |
title | Synthesis, structural characterization, and optical properties of benzo[f]naphtho[2,3-b]phosphoindoles |
title_full | Synthesis, structural characterization, and optical properties of benzo[f]naphtho[2,3-b]phosphoindoles |
title_fullStr | Synthesis, structural characterization, and optical properties of benzo[f]naphtho[2,3-b]phosphoindoles |
title_full_unstemmed | Synthesis, structural characterization, and optical properties of benzo[f]naphtho[2,3-b]phosphoindoles |
title_short | Synthesis, structural characterization, and optical properties of benzo[f]naphtho[2,3-b]phosphoindoles |
title_sort | synthesis, structural characterization, and optical properties of benzo[f]naphtho[2,3-b]phosphoindoles |
topic | Letter |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7940816/ https://www.ncbi.nlm.nih.gov/pubmed/33747236 http://dx.doi.org/10.3762/bjoc.17.56 |
work_keys_str_mv | AT matsumuramio synthesisstructuralcharacterizationandopticalpropertiesofbenzofnaphtho23bphosphoindoles AT teramototakahiro synthesisstructuralcharacterizationandopticalpropertiesofbenzofnaphtho23bphosphoindoles AT kawakubomasato synthesisstructuralcharacterizationandopticalpropertiesofbenzofnaphtho23bphosphoindoles AT kawahatamasatoshi synthesisstructuralcharacterizationandopticalpropertiesofbenzofnaphtho23bphosphoindoles AT muratayuki synthesisstructuralcharacterizationandopticalpropertiesofbenzofnaphtho23bphosphoindoles AT yamaguchikentaro synthesisstructuralcharacterizationandopticalpropertiesofbenzofnaphtho23bphosphoindoles AT uchiyamamasanobu synthesisstructuralcharacterizationandopticalpropertiesofbenzofnaphtho23bphosphoindoles AT yasuikeshuji synthesisstructuralcharacterizationandopticalpropertiesofbenzofnaphtho23bphosphoindoles |