0000000000205632
AUTHOR
Justin J. Dressler
Molecule Isomerism Modulates the Diradical Properties of Stable Singlet Diradicaloids
Inclusion of quinoidal cores in conjugated hydrocarbons is a common strategy to modulate the properties of diradicaloids formed by aromaticity recovery within the quinoidal unit. Here we describe an alternative approach of tuning of diradical properties in indenoindenodibenzothiophenes upon anti → syn isomerism of the benzothiophene motif. This alters the relationship of the S atom with the radical center from linear to cross conjugation yet retains the same 2,6-naphtho conjugation pattern of the rearomatized core. We conduct a full comparison between the anti and syn derivatives based on structural, spectroscopic, theoretical, and magnetic measurements, showing that these systems are stabl…
Diindenoanthracene Diradicaloids Enable Rational, Incremental Tuning of Their Singlet-Triplet Energy Gaps
Summary A fundamental understanding of the inherent electronic and magnetic properties of open-shell diradicaloids is essential so that these properties can be modified to create molecules that meet the potential needs of industry. However, there have been very few attempts to date to systematically accomplish this in diradicaloid compounds. Here, we present the synthetic, spectroscopic, and computational investigation of a series of molecules based on the diindeno[1,2-b:1′,2′-g]anthracene framework. Calculations suggest that by altering the transfer integral term, tab, we are able to manipulate the diradical character and, thus, ΔEST within this series of molecules. Experimentally determin…
Late-Stage Modification of Electronic Properties of Antiaromatic and Diradicaloid Indeno[1,2-b]fluorene Analogues via Sulfur Oxidation
The ability to alter optoelectronic and magnetic properties of molecules at a late stage in their preparation is in general a nontrivial feat. Here, we report the late-stage oxidation of benzothiop...
CCDC 1995028: Experimental Crystal Structure Determination
Related Article: Justin J. Dressler, Joshua E. Barker, Lucas J. Karas, Hannah E. Hashimoto, Ryohei Kishi, Lev N. Zakharov, Samantha N. MacMillan, Carlos J. Gomez-Garcia, Masayoshi Nakano, Judy I. Wu, Michael M. Haley|2020|J.Org.Chem.|85|10846|doi:10.1021/acs.joc.0c01387
CCDC 1949614: Experimental Crystal Structure Determination
Related Article: Justin J. Dressler, Abel Cárdenas Valdivia, Ryohei Kishi, Gabriel E. Rudebusch, Austin M. Ventura, Brian E. Chastain, Carlos J. Gómez-García, Lev N. Zakharov, Masayoshi Nakano, Juan Casado, Michael M. Haley|2020|Cell Press: Chem|6|1353|doi:10.1016/j.chempr.2020.02.010
CCDC 1949404: Experimental Crystal Structure Determination
Related Article: Joshua E. Barker, Justin J. Dressler, Abel Cárdenas Valdivia, Ryohei Kishi, Eric T. Strand, Lev N. Zakharov, Samantha N. MacMillan, Carlos J. Gómez-García, Masayoshi Nakano, Juan Casado, Michael M. Haley|2019|J.Am.Chem.Soc.|142|1548|doi:10.1021/jacs.9b11898
CCDC 1949613: Experimental Crystal Structure Determination
Related Article: Justin J. Dressler, Abel Cárdenas Valdivia, Ryohei Kishi, Gabriel E. Rudebusch, Austin M. Ventura, Brian E. Chastain, Carlos J. Gómez-García, Lev N. Zakharov, Masayoshi Nakano, Juan Casado, Michael M. Haley|2020|Cell Press: Chem|6|1353|doi:10.1016/j.chempr.2020.02.010
CCDC 1994473: Experimental Crystal Structure Determination
Related Article: Justin J. Dressler, Joshua E. Barker, Lucas J. Karas, Hannah E. Hashimoto, Ryohei Kishi, Lev N. Zakharov, Samantha N. MacMillan, Carlos J. Gomez-Garcia, Masayoshi Nakano, Judy I. Wu, Michael M. Haley|2020|J.Org.Chem.|85|10846|doi:10.1021/acs.joc.0c01387
CCDC 1949611: Experimental Crystal Structure Determination
Related Article: Justin J. Dressler, Abel Cárdenas Valdivia, Ryohei Kishi, Gabriel E. Rudebusch, Austin M. Ventura, Brian E. Chastain, Carlos J. Gómez-García, Lev N. Zakharov, Masayoshi Nakano, Juan Casado, Michael M. Haley|2020|Cell Press: Chem|6|1353|doi:10.1016/j.chempr.2020.02.010
CCDC 1949612: Experimental Crystal Structure Determination
Related Article: Justin J. Dressler, Abel Cárdenas Valdivia, Ryohei Kishi, Gabriel E. Rudebusch, Austin M. Ventura, Brian E. Chastain, Carlos J. Gómez-García, Lev N. Zakharov, Masayoshi Nakano, Juan Casado, Michael M. Haley|2020|Cell Press: Chem|6|1353|doi:10.1016/j.chempr.2020.02.010
CCDC 1589136: Experimental Crystal Structure Determination
Related Article: Joshua E. Barker, Justin J. Dressler, Abel Cárdenas Valdivia, Ryohei Kishi, Eric T. Strand, Lev N. Zakharov, Samantha N. MacMillan, Carlos J. Gómez-García, Masayoshi Nakano, Juan Casado, Michael M. Haley|2019|J.Am.Chem.Soc.|142|1548|doi:10.1021/jacs.9b11898
CCDC 1995029: Experimental Crystal Structure Determination
Related Article: Justin J. Dressler, Joshua E. Barker, Lucas J. Karas, Hannah E. Hashimoto, Ryohei Kishi, Lev N. Zakharov, Samantha N. MacMillan, Carlos J. Gomez-Garcia, Masayoshi Nakano, Judy I. Wu, Michael M. Haley|2020|J.Org.Chem.|85|10846|doi:10.1021/acs.joc.0c01387
CCDC 1964314: Experimental Crystal Structure Determination
Related Article: Justin J. Dressler, Abel Cárdenas Valdivia, Ryohei Kishi, Gabriel E. Rudebusch, Austin M. Ventura, Brian E. Chastain, Carlos J. Gómez-García, Lev N. Zakharov, Masayoshi Nakano, Juan Casado, Michael M. Haley|2020|Cell Press: Chem|6|1353|doi:10.1016/j.chempr.2020.02.010
CCDC 1995030: Experimental Crystal Structure Determination
Related Article: Justin J. Dressler, Joshua E. Barker, Lucas J. Karas, Hannah E. Hashimoto, Ryohei Kishi, Lev N. Zakharov, Samantha N. MacMillan, Carlos J. Gomez-Garcia, Masayoshi Nakano, Judy I. Wu, Michael M. Haley|2020|J.Org.Chem.|85|10846|doi:10.1021/acs.joc.0c01387