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 -