Phthalorubines: Fused‐Ring Compounds Synthesized from Phthalonitrile. Issue 47 (25th October 2018)

• Record Type: Journal Article
• Authors: Zheng, Wei; Zhao, Yuan; Zhuang, Wen‐Hao; Wu, Jing‐Jing; Wang, Fang‐Zhou; Li, Cheng‐Hui; Zuo, Jing‐Lin
• Is Part Of: Angewandte Chemie international edition. Volume 57:Issue 47(2018)
• Page Start: 15384
• Page End: 15389
• Publication Date: 2018-10-25
• Subjects: conjugation -- fused rings -- heterocycles -- pigments and dyes -- structure elucidation; Chemistry -- Periodicals; 540
• DOI: 10.1002/anie.201807281
• Languages: English
• ISSNs: 1433-7851

Abstract

Abstract: 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, 1 H 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). Abstract : 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).