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Organosulfur Materials with High Photo- and Photo-Oxidation Stability: 10-Anthryl Sulfoxides and Sulfones and Their Photophysical Properties Dependent on the Sulfur Oxidation State.

ABSTRACT: While few studies show only symmetrical and poorly mono-SO_n (n = 0-2) substituted acenes, in this study, we present a synthesis of a new group of unsymmetrical, significantly substituted derivatives, which revealed unique photophysical properties. Both sulfides (S), sulfoxides (SO) and sulfones (SO₂) showed very high photochemical stabilities, unusual for these groups, during UV-irradiation at 254/365 nm (air O₂ and Ar), which was higher than any found in the literature. For the (S)/(SO) series (254 nm), the stabilities of 80-519 min. (air O₂ and Ar) were found. At 365 nm, stabilities of 124-812 min./(air O₂) for (S)/(SO) and higher for (SO₂) were observed. Photoluminescence lifetimes of (SO_n) of the lower anthryl symmetry remained in the following order: (SO₂) < (S) < (SO); those with full symmetry were in the following order: (S) < (SO) < (SO₂). The enhanced photostability was explained with DFT/MS/Hammett's constants, which showed the leading role of the SO_n groups in stabilization of HOMO/LUMO frontier orbitals. The SO_n (n = 0-2) substituted acenes turned out to be tunable violet/blue/green emitters by oxidation of S atoms and the introduction of rich substitution.

SUBMITTER: Balczewski P

PROVIDER: S-EPMC8269563 | biostudies-literature |

REPOSITORIES: biostudies-literature

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