10,15-<i>Bis</i>(trifluoromethyl)B(III)subchlorin

Bhat, Ishfaq A.; Panda, Pradeepta K.

doi:10.1142/s1088424622500511

J. Porphyrins Phthalocyanines

2022

DOI: 10.1142/s1088424622500511

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10,15-Bis(trifluoromethyl)B(III)subchlorin

Ishfaq A. Bhat

Pradeepta K. Panda

Abstract: Meso-free B(III)subchlorin has been synthesized for the first time using meso-trifluoromethyl substituted tripyrrane, in trace quantity. It displays the most-blue shifted absorption and emission for subchlorins. This macrocycle was found to be completely resistant to oxidation and moderately generate singlet oxygen (34 %).

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Synthesis of Trifluoromethyl-Substituted [14]Triphyrin(2.1.1), Its Selective Reduction to Triphachlorin, and Stable Isomeric Triphabacteriochlorins via Direct Detrifluoromethylation

Bhat

Panda

2022

Org. Lett.

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Two novel classes of reduced triphyrin(2.1.1), namely, triphachlorin and triphabacteriochlorin, are realized via selective reduction of the newly synthesized 7,12-bis-(trifluoromethyl)triphyrin(2.1.1) 1 using p-tosylhydrazide. Triphachlorin 2 displayed red-shifted absorption (580 nm). Harsher conditions, however, led to a unique direct detrifluoromethylation of one CF 3 moiety to form two isomeric triphabacteriochlorins 3 and 4, which exhibit blue-shifted intense lowest-energy absorption bands and intense emission (ϕ f = 0.52 and 0.36, respectively) while generating singlet oxygen very efficiently (ϕ Δ = 0.88 and 0.86, respectively). These reduced porphyrinoids show very high oxidative stability as they remain unchanged upon refluxing with 2,3-dichloro-5,6-dicyanobenzoquinone in toluene.

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Synthesis of Trifluoromethyl-Substituted [14]Triphyrin(2.1.1), Its Selective Reduction to Triphachlorin, and Stable Isomeric Triphabacteriochlorins via Direct Detrifluoromethylation

Bhat

Panda

2022

Org. Lett.

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10,15-Bis(trifluoromethyl)B(III)subchlorin

Cited by 1 publication

References 7 publications

Synthesis of Trifluoromethyl-Substituted [14]Triphyrin(2.1.1), Its Selective Reduction to Triphachlorin, and Stable Isomeric Triphabacteriochlorins via Direct Detrifluoromethylation

Synthesis of Trifluoromethyl-Substituted [14]Triphyrin(2.1.1), Its Selective Reduction to Triphachlorin, and Stable Isomeric Triphabacteriochlorins via Direct Detrifluoromethylation

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