A simple synthesis of symmetric phthalocyanines and their respective perfluoro and transition‐metal complexes. (13th March 2019)

• Record Type: Journal Article
• Authors: Denekamp, Ilse M.; Veenstra, Florentine L.P.; Jungbacker, Peter; Rothenberg, Gadi
• Is Part Of: Applied organometallic chemistry. Volume 33:Number 5(2019)
• Page Start: n/a
• Page End: n/a
• Publication Date: 2019-03-13
• Subjects: macrocycles -- metalation -- NMR -- one step synthesis -- sustainable chemistry; Organometallic chemistry -- Periodicals; Organometallic compounds -- Periodicals; 547.05
• DOI: 10.1002/aoc.4872
• Languages: English
• ISSNs: 0268-2605

Abstract

Abstract : We report a simple synthesis protocol for making phthalocyanines (Pcs) starting from phthalonitriles. This method is general and requires no specialised equipment. The complexes are isolated and characterised using X‐ray diffraction, NMR, FTIR and Raman spectroscopy and high‐resolution mass spectrometry. First, we study and present a one‐step synthesis route to a metal‐free Pc (H2 PcH16 ), as well as to the corresponding MPcH16 complexes of Mn, Fe, Co, Ni, Cu and Zn. Then, we show that this route can also be used to make the fluorinated Pc analogues (MPcF16 ). Finally, we present a new and useful procedure for inserting a metal ion into a metal‐free H2 PcH16 ring, by direct metalation, yielding the corresponding MPcH16 complex. This last method is especially useful if you want to make different MPcH16 complexes. Abstract : Step up! We present a one‐step synthesis to metal‐free and metal‐containing phthalocyanines and the fluorinated metal‐Pc analogues, as well as a simple procedure for inserting a metal ion into an metal‐free Pc ring.