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Phthalorubines: Fused-Ring Compounds Synthesized from Phthalonitrile
Nanjing Univ, Collaborat Innovat Ctr Adv Microstruct, Nanjing Natl Lab Microstruct, Sch Chem & Chem Engn,State Key Lab Coordinat Chem, Nanjing 210093, Jiangsu, Peoples R China.
Henan Univ, Key Lab Nat Med & Immunoengn, Kaifeng 475004, Peoples R China.
Nanjing Univ, Collaborat Innovat Ctr Adv Microstruct, Nanjing Natl Lab Microstruct, Sch Chem & Chem Engn,State Key Lab Coordinat Chem, Nanjing 210093, Jiangsu, Peoples R China.
Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - Ångström. Xiamen Univ, Coll Chem & Chem Engn, Xiamen 361005, Peoples R China.
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2018 (English)In: Angewandte Chemie International Edition, ISSN 1433-7851, E-ISSN 1521-3773, Vol. 57, no 47, p. 15384-15389Article in journal (Refereed) Published
Abstract [en]

A series of dibenzo[a, fll1,3,5] 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, H-1 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 pi-pi* 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).

Place, publisher, year, edition, pages
WILEY-V C H VERLAG GMBH , 2018. Vol. 57, no 47, p. 15384-15389
Keywords [en]
conjugation, fused rings, heterocycles, pigments and dyes, structure elucidation
National Category
Organic Chemistry
Identifiers
URN: urn:nbn:se:uu:diva-372819DOI: 10.1002/anie.201807281ISI: 000453344500012PubMedID: 30251399OAI: oai:DiVA.org:uu-372819DiVA, id: diva2:1277050
Available from: 2019-01-09 Created: 2019-01-09 Last updated: 2019-01-09Bibliographically approved

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