0000000001300649
AUTHOR
Abel Cárdenas Valdivia
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…
Monoradicals and Diradicals of Dibenzofluoreno[3,2-b]fluorene Isomers: Mechanisms of Electronic Delocalization
The preparation of a series of dibenzo- and tetrabenzo-fused fluoreno[3,2-b]fluorenes is disclosed, and the diradicaloid properties of these molecules are compared with those of a similar, previously reported series of anthracene-based diradicaloids. Insights on the diradical mode of delocalization tuning by constitutional isomerism of the external naphthalenes has been explored by means of the physical approach (dissection of the electronic properties in terms of electronic repulsion and transfer integral) of diradicals. This study has also been extended to the redox species of the two series of compounds and found that the radical cations have the same stabilization mode by delocalization…
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…
CCDC 2016988: Experimental Crystal Structure Determination
Related Article: Hideki Hayashi, Joshua E. Barker, Abel Cárdenas Valdivia, Ryohei Kishi, Samantha N. MacMillan, Carlos J. Gómez-García, Hidenori Miyauchi, Yosuke Nakamura, Masayoshi Nakano, Shin-ichiro Kato, Michael M. Haley, Juan Casado|2020|J.Am.Chem.Soc.|142|20444|doi:10.1021/jacs.0c09588
CCDC 2023797: Experimental Crystal Structure Determination
Related Article: Hideki Hayashi, Joshua E. Barker, Abel Cárdenas Valdivia, Ryohei Kishi, Samantha N. MacMillan, Carlos J. Gómez-García, Hidenori Miyauchi, Yosuke Nakamura, Masayoshi Nakano, Shin-ichiro Kato, Michael M. Haley, Juan Casado|2020|J.Am.Chem.Soc.|142|20444|doi:10.1021/jacs.0c09588
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 2016990: Experimental Crystal Structure Determination
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CCDC 2016987: Experimental Crystal Structure Determination
Related Article: Hideki Hayashi, Joshua E. Barker, Abel Cárdenas Valdivia, Ryohei Kishi, Samantha N. MacMillan, Carlos J. Gómez-García, Hidenori Miyauchi, Yosuke Nakamura, Masayoshi Nakano, Shin-ichiro Kato, Michael M. Haley, Juan Casado|2020|J.Am.Chem.Soc.|142|20444|doi:10.1021/jacs.0c09588
CCDC 2016986: Experimental Crystal Structure Determination
Related Article: Hideki Hayashi, Joshua E. Barker, Abel Cárdenas Valdivia, Ryohei Kishi, Samantha N. MacMillan, Carlos J. Gómez-García, Hidenori Miyauchi, Yosuke Nakamura, Masayoshi Nakano, Shin-ichiro Kato, Michael M. Haley, Juan Casado|2020|J.Am.Chem.Soc.|142|20444|doi:10.1021/jacs.0c09588
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 2016989: Experimental Crystal Structure Determination
Related Article: Hideki Hayashi, Joshua E. Barker, Abel Cárdenas Valdivia, Ryohei Kishi, Samantha N. MacMillan, Carlos J. Gómez-García, Hidenori Miyauchi, Yosuke Nakamura, Masayoshi Nakano, Shin-ichiro Kato, Michael M. Haley, Juan Casado|2020|J.Am.Chem.Soc.|142|20444|doi:10.1021/jacs.0c09588
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 2016622: Experimental Crystal Structure Determination
Related Article: Hideki Hayashi, Joshua E. Barker, Abel Cárdenas Valdivia, Ryohei Kishi, Samantha N. MacMillan, Carlos J. Gómez-García, Hidenori Miyauchi, Yosuke Nakamura, Masayoshi Nakano, Shin-ichiro Kato, Michael M. Haley, Juan Casado|2020|J.Am.Chem.Soc.|142|20444|doi:10.1021/jacs.0c09588
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