First examples of functionalisation of  meso -aryl tetrabenzotriazaporphyrins (TBTAPs) through cross-coupling reactions

Alharbi, Nuha; Tizzard, Graham J.; Coles, Simon J.; Cook, Michael J.; Cammidge, Andrew N.

doi:10.1016/j.tet.2015.03.095

Cited by 3 publications

(2 citation statements)

References 14 publications

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“…With the exception of these three examples, the tetrabenzo-annulated derivatives (TBTrAPs) are the only other azaporphyrins containing three meso -nitrogen atoms to have been reported in the literature. Cammidge and co-workers recently reported an efficient protocol for the synthesis of TBTrAPs. − According to this process, the desired magnesium(II) complexes of tetrabenzo-TrAPs were prepared in 8–40% yields by heating a mixture of an aminoisoindoline, phthalonitrile, and MgBr 2 in diglyme at 220 °C, followed by the treatment of the resulting intermediate with 1,4-diazabicyclo[2.2.2]octane (DABCO) (Scheme ). The same group also reported the improved synthesis of subtribenzodiazaporphyrins using a similar method …”

Section: Azaporphyrins and Related Compoundsmentioning

confidence: 99%

Synthesis of Aza-, Oxa-, and Thiaporphyrins and Related Compounds

Matano

2016

Chem. Rev.

117

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Chemical modification at the periphery with nitrogen or chalcogens is a highly promising strategy to diversify the optical, electrochemical, magnetic, and coordination properties of the porphyrin family. Indeed, various kinds of phthalocyanines and related benzo-annelated azaporphyrinoids have been synthesized, and their fundamental properties have been extensively investigated. However, the synthesis of heteroatom-containing porphyrins in which the peripheral methine groups are partially replaced with nitrogen or chalcogens remains a considerable challenge. In this review, we will focus mainly on recent advances in the synthesis of aza-, oxa-, and thiaorphyrins and related compounds, including historically important examples.

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Section: Azaporphyrins and Related Compoundsmentioning

confidence: 99%

Synthesis of Aza-, Oxa-, and Thiaporphyrins and Related Compounds

Matano

2016

Chem. Rev.

117

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“…The main drawback for TBTAPs, and other hybrid structures, has been the lack of reliable and versatile synthetic strategies to afford them (especially when compared to porphyrins and phthalocyanines). In the last decades, our group and others have developed and studied new synthetic routes, significantly overcoming the initial issues [8][9][10][11][12][13][14][15][16][17][18][19]. Most recently we have disclosed additional control in the synthesis of TBTAPs that permits direct access to meso-aryl 3:1 (ABBB-Ar) and 2:2 (ABBA-Ar) derivatives [20].…”

Section: Introductionmentioning

confidence: 99%

Convenient syntheses of phthalocyanine and tetrabenzotriazaporphyrin (TBTAP) mono-alkynes; unhindered building blocks for click chemistry and beyond

Aljuhani

Díaz‐Moscoso

Cammidge

2023

J. Porphyrins Phthalocyanines

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Unsymmetrical phthalocyanines and related macrocycles are often desirable for covalent construction or the self-assembly of more complex architectures. Terminal alkynes are versatile in this regard because they are amenable to cross-coupling via Sonogashira-type reactions, alkyne-alkyne coupling via Glaser-type couplings, and triazole formation via Click reaction with azides. Here we describe two complementary syntheses to conveniently add a single alkyne onto the phthalocyanine peripheral position and onto the meso-phenyl group of an (aryl)tetrabenzotriazaporphyrin, here providing a remote link point that is insulated from the macrocycle.

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Meso‐Substituted Tetrabenzotriazaporphyrins for Dye‐Sensitized Solar Cells

Tejerina

Yamamoto

López‐Duarte

et al. 2020

Helvetica Chimica Acta

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A novel tetrabenzotriazaporphyrin (TBTAP) bearing an anchoring carboxy‐phenyl group at the meso‐carbon position (TT260) was synthesized by an efficient method, which involves the crossover condensation between phthalonitrile and aminoisoindoline precursors. Its optical and electrochemical properties were also investigated together with its use as sensitizer in dye‐sensitized solar cells (DSSCs). The performance of TT260 was compared with a benchmark molecule TT1, bearing similar bulky tert‐butyl groups at the periphery. The device, which is the first ever example of meso‐substituted TBTAP‐based DSSC, exhibits a modest maximum power conversion efficiency of 2.4±0.1 % under one‐sun conditions.

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First examples of functionalisation of meso -aryl tetrabenzotriazaporphyrins (TBTAPs) through cross-coupling reactions

Cited by 3 publications

References 14 publications

Synthesis of Aza-, Oxa-, and Thiaporphyrins and Related Compounds

Synthesis of Aza-, Oxa-, and Thiaporphyrins and Related Compounds

Convenient syntheses of phthalocyanine and tetrabenzotriazaporphyrin (TBTAP) mono-alkynes; unhindered building blocks for click chemistry and beyond

Meso‐Substituted Tetrabenzotriazaporphyrins for Dye‐Sensitized Solar Cells

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