Details
| Original language | English |
|---|---|
| Pages (from-to) | 6319-6333 |
| Number of pages | 15 |
| Journal | European Journal of Organic Chemistry |
| Volume | 2021 |
| Issue number | 46 |
| Early online date | 3 Sept 2021 |
| Publication status | Published - 9 Dec 2021 |
Abstract
Quinones have widespread applications in view of their interesting chemical and photophysical features. On the other hand, benzocyclobutenes (BCBs) are generally masked reactive dienes suitable for the [4+2] cycloaddition reactions. Here, benzocyclobutenes and benzodicyclobutenes (BDCBs) were prepared and further reacted with benzoquinone and naphthoquinone in order to obtain some new polycyclic quinones with highly extended π systems, namely, 6-bromo-5,8-dimethoxyanthracene-1,4-dione, 2,9-dibromo-1,4,8,11-tetramethoxypentacene-6,13-dione, 9-bromo-7,10-dimethoxytetracene-5,12-dione, 3,10-dimethoxycyclobuta[b]anthracene-1,5,8(2H)-trione, 6,10,17,21-tetramethoxynonacene-1,4,8,12,15,19-hexaone, and 3,12-dimethoxycyclobuta[b]tetracene-1,5,10(2H)-trione. In addition to their spectroscopic characterization the new compounds are investigated by UV and fluorescence spectroscopy, cyclic voltammetry, and DFT calculations.
Keywords
- Benzocyclobutenes, Bidirectional acene synthesis, Cycloaddition, Photophysical properties, Quinones
ASJC Scopus subject areas
- Chemistry(all)
- Physical and Theoretical Chemistry
- Chemistry(all)
- Organic Chemistry
Cite this
- Standard
- Harvard
- Apa
- Vancouver
- BibTeX
- RIS
In: European Journal of Organic Chemistry, Vol. 2021, No. 46, 09.12.2021, p. 6319-6333.
Research output: Contribution to journal › Article › Research › peer review
}
TY - JOUR
T1 - Bidirectional Synthesis, Photophysical and Electrochemical Characterization of Polycyclic Quinones Using Benzocyclobutenes and Benzodicyclobutenes as Precursors
AU - Abdelmoniem, Amr Mohamed
AU - Abdelshafy Abdelhamid, Ismail
AU - Butenschön, Holger
N1 - Funding Information: Both Amr M. Abdelmoniem and Ismail A. Abdelhamid acknowledge the Alexander von Humboldt Foundation for a Georg Forster and an Alexander von Humboldt research fellowship, respectively. We thank Mr. Patrick Bessel, M. Sc., and Mr. Pascal Rusch, M. Sc., Institut für Physikalische Chemie und Elektrochemie, Leibniz Universität Hannover, for their help in measuring UV and fluorescence spectra, respectively. We are indebted to Prof. Dr. Andreas Pich, Medizinische Hochschule Hannover, for performing the MALDI measurement of . Open Access funding enabled and organized by Projekt DEAL. 40
PY - 2021/12/9
Y1 - 2021/12/9
N2 - Quinones have widespread applications in view of their interesting chemical and photophysical features. On the other hand, benzocyclobutenes (BCBs) are generally masked reactive dienes suitable for the [4+2] cycloaddition reactions. Here, benzocyclobutenes and benzodicyclobutenes (BDCBs) were prepared and further reacted with benzoquinone and naphthoquinone in order to obtain some new polycyclic quinones with highly extended π systems, namely, 6-bromo-5,8-dimethoxyanthracene-1,4-dione, 2,9-dibromo-1,4,8,11-tetramethoxypentacene-6,13-dione, 9-bromo-7,10-dimethoxytetracene-5,12-dione, 3,10-dimethoxycyclobuta[b]anthracene-1,5,8(2H)-trione, 6,10,17,21-tetramethoxynonacene-1,4,8,12,15,19-hexaone, and 3,12-dimethoxycyclobuta[b]tetracene-1,5,10(2H)-trione. In addition to their spectroscopic characterization the new compounds are investigated by UV and fluorescence spectroscopy, cyclic voltammetry, and DFT calculations.
AB - Quinones have widespread applications in view of their interesting chemical and photophysical features. On the other hand, benzocyclobutenes (BCBs) are generally masked reactive dienes suitable for the [4+2] cycloaddition reactions. Here, benzocyclobutenes and benzodicyclobutenes (BDCBs) were prepared and further reacted with benzoquinone and naphthoquinone in order to obtain some new polycyclic quinones with highly extended π systems, namely, 6-bromo-5,8-dimethoxyanthracene-1,4-dione, 2,9-dibromo-1,4,8,11-tetramethoxypentacene-6,13-dione, 9-bromo-7,10-dimethoxytetracene-5,12-dione, 3,10-dimethoxycyclobuta[b]anthracene-1,5,8(2H)-trione, 6,10,17,21-tetramethoxynonacene-1,4,8,12,15,19-hexaone, and 3,12-dimethoxycyclobuta[b]tetracene-1,5,10(2H)-trione. In addition to their spectroscopic characterization the new compounds are investigated by UV and fluorescence spectroscopy, cyclic voltammetry, and DFT calculations.
KW - Benzocyclobutenes
KW - Bidirectional acene synthesis
KW - Cycloaddition
KW - Photophysical properties
KW - Quinones
UR - http://www.scopus.com/inward/record.url?scp=85115259884&partnerID=8YFLogxK
U2 - 10.1002/ejoc.202100848
DO - 10.1002/ejoc.202100848
M3 - Article
AN - SCOPUS:85115259884
VL - 2021
SP - 6319
EP - 6333
JO - European Journal of Organic Chemistry
JF - European Journal of Organic Chemistry
SN - 1434-193X
IS - 46
ER -