A Friedl?nder route to 5,7-diazapentacenes?
Journal of Materials Chemistry C Pub Date: 2018-01-03 DOI: 10.1039/C7TC05057G
Abstract
A route to compounds with a 5,7-diazapentacene skeleton has been established involving a Friedl?nder reaction. A diaminodiketone 8 has been made by a novel method and reacted with cyclohexanone to prepare an octa-hydro-5,7-diazapentacene 7a and with tetralone to produce a dibenzotetrahydro-5,7-diazapentacene 7b. Reaction of the diaminodiketone with a diarylethanone followed by oxidation gave a tetrabenzo-5,7-diazapentacene 18b. Compound 7b undergoes solid-state dimerization during single-crystal X-ray analysis. These materials possess lower frontier orbitals than pentacene and show strong absorption and fluorescence which is affected by the presence of acid. In particular 18b shows a remarkable colour change in solution upon addition of acid. These results suggest that suitably functionalised 5,7-diazapentacenes could be promising candidates for optoelectronic applications.
Recommended Literature
- [1] Evolution of cellulose into flexible conductive green electronics: a smart strategy to fabricate sustainable electrodes for supercapacitors Tengfei Yu,Yuehan Wu,Wei Li,Bin LiRSC Adv., 2014,4, 34134-34143 10.1039/C4RA07017H
- [2] Emerging investigator series: first-principles and thermodynamics comparison of compositionally-tuned delafossites: cation release from the (001) surface of complex metal oxides? Joseph W. Bennett,Diamond T. Jones,Blake G. Hudson,Joshua Melendez-Rivera,Robert J. Hamers,Sara E. MasonEnviron. Sci.: Nano, 2020,7, 1642-1651 10.1039/C9EN01304K
- [3] Excellent kinetics of single-phase Gd-doped ceria fuel electrodes in solid oxide cells? Andreas Nenning,Manuel Holzmann,Jürgen Fleig,Alexander K. OpitzMater. Adv., 2021,2, 5422-5431 10.1039/D1MA00202C
- [4] Embedding cyclic nitrone in mesoporous silica particles for EPR spin trapping of superoxide and other radicals? Eric Besson,Stéphane Gastaldi,Emily Bloch,Selma Aslan,Hakim Karoui,Olivier Ouari,Micael HardyAnalyst, 2019,144, 4194-4203 10.1039/C9AN00468H
- [5] Ester-directed orthogonal dual C–H activation and ortho aryl C–H alkenylation via distal weak coordination? Manickam Bakthadoss,Tadiparthi Thirupathi Reddy,Vishal Agarwal,Duddu S. SharadaChem. Commun., 2022,58, 1406-1409 10.1039/D1CC06097J
- [6] Empowering microfluidics by micro-3D printing and solution-based mineral coating? Hongxia Li,Aikifa Raza,Qiaoyu Ge,Jin-You Lu,TieJun ZhangSoft Matter, 2020,16, 6841-6849 10.1039/D0SM00958J
- [7] Establishing plasmon contribution to chemical reactions: alkoxyamines as a thermal probe? Olga Guselnikova,Gérard Audran,Jean-Patrick Joly,Andrii Trelin,Evgeny V. Tretyakov,Vaclav Svorcik,Oleksiy Lyutakov,Sylvain R. A. MarqueChem. Sci., 2021,12, 4154-4161 10.1039/D0SC06470J
- [8] Fatty acid eutectic mixtures and derivatives from non-edible animal fat as phase change materials? Pau Gallart-Sirvent,Marc Martín,Gemma Villorbina,Mercè Balcells,Aran Solé,Luisa F. Cabeza,Ramon Canela-GarayoaRSC Adv., 2017,7, 24133-24139 10.1039/C7RA03845C
- [9] Evolution of important glucosinolates in three common Brassica vegetables during their processing into vegetable powder and in vitro gastric digestion Nan Fu,Naphaporn Chiewchan,Xiao Dong ChenFood Funct., 2020,11, 211-220 10.1039/C9FO00811J
- [10] Fe(iii)-mediated isomerization of α,α-diarylallylic alcohols to ketones via radical 1,2-aryl migration? Ziyang Deng,Changwei Chen,Sunliang CuiRSC Adv., 2016,6, 93753-93755 10.1039/C6RA20007A
Journal Name：Journal of Materials Chemistry C
research_products
-
CAS no.: 89640-58-4
![1,2,3,4,5,6-Hexahydro-[2,3]bipyridinyl-6-ol](https://ossimg.kuujia.com/scimg/1271000/1270529-38-8x500.png)
![N-(3-cyanothiolan-3-yl)-2-[(2,2,2-trifluoroethyl)sulfanyl]pyridine-4-carboxamide](https://ossimg.kuujia.com/scimg/1444500/1444113-98-7x500.png)
![2,2-Difluoro-3-[methyl(2-methylbutyl)amino]propanoic acid](https://ossimg.kuujia.com/scimg/2138500/2138166-62-6x500.png)
![2-(1H-indol-3-yl)-N-{[6-(thiophen-2-yl)-[1,2,4]triazolo[4,3-b]pyridazin-3-yl]methyl}acetamide](https://ossimg.kuujia.com/scimg/2034500/2034271-14-0x500.png)