Phthalorubines: Fused‐Ring Compounds Synthesized from Phthalonitrile

• Published in: Angewandte Chemie International Edition Vol. 57; no. 47; pp. 15384 - 15389
• Main Authors: Zheng, Wei, Zhao, Yuan, Zhuang, Wen‐Hao, Wu, Jing‐Jing, Wang, Fang‐Zhou, Li, Cheng‐Hui, Zuo, Jing‐Lin
• Format: Journal Article
• Language: English
• Published: WEINHEIM Wiley 19.11.2018; Wiley Subscription Services, Inc
• Edition: International ed. in English
• Subjects: Aromatic compounds; Chemistry; Chemistry, Multidisciplinary; conjugation; Crystallography; Cyclic compounds; Energy absorption; fused rings; heterocycles; Magnetic resonance spectroscopy; NMR spectroscopy; Nomenclature; Physical Sciences; pigments and dyes; Porphyrins; Science & Technology; structure elucidation; Synthesis; X ray spectra; fused rings; pigments and dyes; DESIGN; FACILE SYNTHESIS; BENZIPHTHALOCYANINE; heterocycles; CENTERED TEMPLATE REACTIONS; PHTHALOCYANINE; COMPLEXES; structure elucidation; conjugation
• ISSN: 1433-7851; 1521-3773; 1521-3773
• DOI: 10.1002/anie.201807281

A series of dibenzo[a,f][1,3,5]triazino[2,1,6‐cd] pyrrolizine compounds have been synthesized from phthalonitriles by a facile intramolecular cyclization process using “half‐phthalocyanine” precursors, and they were characterized by X‐ray crystallography, 1H NMR spectroscopy, UV/Vis, and theoretical calculations. These compounds have spectroscopic profiles similar to phthalocyanines and porphyrins, although their inner‐core structures and coordination types are totally different. They can be regarded as a new class of aromatic fused‐ring compounds. The low‐energy absorption of these new fused‐ring compounds are located at around 600 nm. Such a low‐energy π–π* transition is scarce in aromatic compounds having a similar molecular size. According to the nomenclature of phthalocyanines, these types of compounds have been named phthalorubines (Prs). Ruby red: A new class of fused‐ring compounds has been synthesized from phthalonitrile. These compounds have very similar spectroscopic profiles as phthalocyanines, but have a very different inner‐core structure and coordination properties. According to the nomenclature of phthalocyanines, these compounds have been named as phthalorubines (Prs).