0000000001300656
AUTHOR
Michael M. Haley
showing 30 related works from this author
Molecule Isomerism Modulates the Diradical Properties of Stable Singlet Diradicaloids
2019
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…
Diindeno-fusion of an anthracene as a design strategy for stable organic biradicals
2016
The consequence of unpaired electrons in organic molecules has fascinated and confounded chemists for over a century. The study of open-shell molecules has been rekindled in recent years as new synthetic methods, improved spectroscopic techniques and powerful computational tools have been brought to bear on this field. Nonetheless, it is the intrinsic instability of the biradical species that limits the practicality of this research. Here we report the synthesis and characterization of a molecule based on the diindeno[b,i]anthracene framework that exhibits pronounced open-shell character yet possesses remarkable stability. The synthetic route is rapid, efficient and possible on the gram sca…
Monoradicals and Diradicals of Dibenzofluoreno[3,2-b]fluorene Isomers: Mechanisms of Electronic Delocalization
2020
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
2020
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…
A Tale of Two Isomers: Enhanced Antiaromaticity/Diradical Character versus Deleterious Ring‐Opening of Benzofuran‐fused s ‐Indacenes and Dicyclopenta…
2021
We examine the effects of fusing two benzofurans to s-indacene (indacenodibenzofurans, IDBFs) and dicyclopenta[b,g]naphthalene (indenoindenodibenzofurans, IIDBFs) to control the strong antiaromaticity and diradical character of these core units. Synthesis via 3-functionalized benzofuran yields syn-IDBF and syn-IIDBF. syn-IDBF possesses a high degree of paratropicity, exceeding that of the parent hydrocarbon, which in turn results in strong diradical character for syn-IIDBF. In the case of the anti-isomers, synthesized via 2-substituted benzofurans, these effects are decreased; however, both derivatives undergo an unexpected ring-opening reaction during the final dearomatization step. All th…
Late-Stage Modification of Electronic Properties of Antiaromatic and Diradicaloid Indeno[1,2-b]fluorene Analogues via Sulfur Oxidation
2020
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 2016988: Experimental Crystal Structure Determination
2020
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CCDC 1995028: Experimental Crystal Structure Determination
2020
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 2077070: Experimental Crystal Structure Determination
2021
Related Article: Joshua E. Barker, Tavis W. Price, Lucas J. Karas, Ryohei Kishi, Samantha N. MacMillan, Lev N. Zakharov, Carlos J. G��mez���Garc��a, Judy I. Wu, Masayoshi Nakano, Michael M. Haley|2021|Angew.Chem.,Int.Ed.|60|22385|doi:10.1002/anie.202107855
CCDC 2023797: Experimental Crystal Structure Determination
2020
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CCDC 1949614: Experimental Crystal Structure Determination
2020
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CCDC 1949404: Experimental Crystal Structure Determination
2020
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CCDC 1949613: Experimental Crystal Structure Determination
2020
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CCDC 2016990: Experimental Crystal Structure Determination
2020
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CCDC 1994473: Experimental Crystal Structure Determination
2020
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CCDC 2077067: Experimental Crystal Structure Determination
2021
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CCDC 2016987: Experimental Crystal Structure Determination
2020
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CCDC 2016986: Experimental Crystal Structure Determination
2020
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CCDC 1949611: Experimental Crystal Structure Determination
2020
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
2020
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CCDC 1949612: Experimental Crystal Structure Determination
2020
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CCDC 2076414: Experimental Crystal Structure Determination
2021
Related Article: Joshua E. Barker, Tavis W. Price, Lucas J. Karas, Ryohei Kishi, Samantha N. MacMillan, Lev N. Zakharov, Carlos J. G��mez���Garc��a, Judy I. Wu, Masayoshi Nakano, Michael M. Haley|2021|Angew.Chem.,Int.Ed.|60|22385|doi:10.1002/anie.202107855
CCDC 1589136: Experimental Crystal Structure Determination
2020
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CCDC 2016622: Experimental Crystal Structure Determination
2020
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CCDC 1995029: Experimental Crystal Structure Determination
2020
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CCDC 1964314: Experimental Crystal Structure Determination
2020
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CCDC 2077069: Experimental Crystal Structure Determination
2021
Related Article: Joshua E. Barker, Tavis W. Price, Lucas J. Karas, Ryohei Kishi, Samantha N. MacMillan, Lev N. Zakharov, Carlos J. G��mez���Garc��a, Judy I. Wu, Masayoshi Nakano, Michael M. Haley|2021|Angew.Chem.,Int.Ed.|60|22385|doi:10.1002/anie.202107855
CCDC 2077068: Experimental Crystal Structure Determination
2021
Related Article: Joshua E. Barker, Tavis W. Price, Lucas J. Karas, Ryohei Kishi, Samantha N. MacMillan, Lev N. Zakharov, Carlos J. G��mez���Garc��a, Judy I. Wu, Masayoshi Nakano, Michael M. Haley|2021|Angew.Chem.,Int.Ed.|60|22385|doi:10.1002/anie.202107855
CCDC 1995030: Experimental Crystal Structure Determination
2020
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CCDC 1426708: Experimental Crystal Structure Determination
2016
Related Article: Gabriel E. Rudebusch, José L. Zafra, Kjell Jorner, Kotaro Fukuda, Jonathan L. Marshall, Iratxe Arrechea-Marcos, Guzmán L. Espejo, Rocío Ponce Ortiz, Carlos J. Gómez-García, Lev N. Zakharov, Masayoshi Nakano, Henrik Ottosson, Juan Casado, Michael M. Haley|2016|Nature Chemistry|8|753|doi:10.1038/nchem.2518