Photoinduced Changes in Aromaticity Facilitate Electrocyclization of Dithienylbenzene Switches was written by Oruganti, Baswanth;Pal Kalapos, Peter;Bhargav, Varada;London, Gabor;Durbeej, Bo. And the article was included in Journal of the American Chemical Society in 2020.Electric Literature of C6H8S The following contents are mentioned in the article:
The concepts of excited-state aromaticity and antiaromaticity have in recent years been invoked to rationalize the photochem. of cyclic conjugated organic compounds, with the long-term goal of using these concepts to improve the reactivities of such compounds toward different photochem. transformations. It is of particular interest to assess how the presence of a benzene motif affects photochem. reactivity, as benzene is well-known to completely change its aromatic character in its lowest excited states. Here, we investigate how a benzene motif influences the photoinduced electrocyclization of dithienylethenes, a major class of mol. switches. Specifically, we report on the synthesis of a dithienylbenzene switch where the typical nonaromatic, ethene-like motif bridging the two thienyl units is replaced by a benzene motif, and show that this compound undergoes electrocyclization upon irradiation with UV-light. Furthermore, through a detailed quantum chem. anal., we demonstrate that the electrocyclization is driven jointly and synergistically by the loss of aromaticity in this motif from the formation of a reactive, antiarom. excited state during the initial photoexcitation, and by the subsequent relief of this antiaromaticity as the reaction progresses from the Franck-Condon region. Overall, we conclude that photoinduced changes in aromaticity facilitate the electrocyclization of dithienylbenzene switches. This study involved multiple reactions and reactants, such as 2,5-Dimethylthiophene (cas: 638-02-8Electric Literature of C6H8S).
2,5-Dimethylthiophene (cas: 638-02-8) belongs to benzothiophene derivatives. Functionalized benzothiophenes are important constructs found in molecules with wide ranging biological activity and in organic materials. It is found within the chemical structures of pharmaceutical drugs such as zileuton, raloxifene, and sertaconazole, and also BTCP.Electric Literature of C6H8S
Referemce:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem