Photodeoxygenation of phenanthro[4,5-<i>bcd</i>]thiophene <i>S</i>-oxide, triphenyleno[1,12-<i>bcd</i>]thiophene <i>S</i>-oxide and perylo[1,12-<i>bcd</i>]thiophene <i>S</i>-oxide Satyanarayana M. Chintala John T. Petroff II Andrew Barnes Ryan D. McCulla 10.6084/m9.figshare.8152544.v1 https://tandf.figshare.com/articles/journal_contribution/Photodeoxygenation_of_phenanthro_4_5-_i_bcd_i_thiophene_i_S_i_-oxide_triphenyleno_1_12-_i_bcd_i_thiophene_i_S_i_-oxide_and_perylo_1_12-_i_bcd_i_thiophene_i_S_i_-oxide/8152544 <p>Sulfoxides, upon irradiation with ultraviolet (UV) light undergo α-cleavage, hydrogen abstraction, photodeoxygenation, bimolecular photoreduction, and stereo-mutation. The UV irradiation of dibenzothiophene <i>S</i>-oxide (DBTO) yields dibenzothiophene (DBT) as a major product along with ground-state atomic oxygen [O(<sup>3</sup>P)]. This is a common method for generating O(<sup>3</sup>P) in solution. The low quantum yield of photodeoxygenation and the requirement of UVA light are drawbacks of using this method. The sulfoxides benzo[<i>b</i>]naphtho-[1,2,<i>d</i>]thiophene <i>S</i>-oxide, benzo[<i>b</i>]naphtho [2,1,<i>d</i>]thiophene <i>S</i>-oxide, benzo[<i>b</i>] phenanthro[9,10-<i>d</i>]thiophene <i>S</i>-oxide, dinaphtho- [2,1-<i>b</i>:1’,2’-<i>d</i>]thiophene <i>S</i>-oxide, and dinaphtho[1,2-<i>b</i>:2’,1’-<i>d</i>]thiophene <i>S</i>-oxide have shown to deoxygenate up to three times faster than DBTO upon UVA irradiation; however, the photodeoxygenation of these sulfoxides does not appear to be limited to the production of O(<sup>3</sup>P). In this work, phenanthro[4,5-<i>bcd</i>]thiophene <i>S</i>-oxide, triphenyleno[1,12-<i>bcd</i>]thiophene-<i>S</i>-oxide, and perylo[1,12-<i>bcd</i>]thiophene-<i>S</i>-oxide were synthesized and their photodeoxygenation was studied. Phenanthro[4,5-<i>bcd</i>]thiophene-<i>S</i>-oxide, triphenyleno[1,12-<i>bcd</i>]thiophene-<i>S</i>-oxide, and perylo[1,12-<i>bcd</i>]thiophene-<i>S</i>-oxide deoxygenated upon UVA irradiation. However, the common intermediate experiments did not conclusively identify the photodeoxygenation mechanism of these sulfoxides.</p> 2019-05-20 05:59:34 Photodeoxygenation sulfoxides reactive oxygen species triplet oxygen toluene oxidation 1-octene oxidation polycyclic sulfoxide