0000000001301747

AUTHOR

Justin J. Dressler

showing 14 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…

ChemistryDiradicalBenzothiopheneAromaticityGeneral ChemistryConjugated system010402 general chemistryPhotochemistry01 natural sciencesBiochemistryCatalysis0104 chemical scienceschemistry.chemical_compoundColloid and Surface ChemistryMoleculeSinglet stateCross-conjugationTriplet stateJournal of the American Chemical Society
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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…

PhysicsSeries (mathematics)DiradicalMagnetometerGeneral Chemical EngineeringBiochemistry (medical)02 engineering and technologyGeneral Chemistry010402 general chemistry021001 nanoscience & nanotechnology01 natural sciencesBiochemistry0104 chemical scienceslaw.inventionSQUIDChemical physicslawMaterials ChemistryEnvironmental ChemistryMoleculeSinglet state0210 nano-technologyEnergy (signal processing)Chem
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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...

010405 organic chemistryChemistryOrganic ChemistryLate stagechemistry.chemical_elementFluoreneequipment and supplies010402 general chemistryPhotochemistry01 natural sciencesSulfur0104 chemical scienceschemistry.chemical_compoundMoleculehuman activitiesAntiaromaticityElectronic propertiesThe Journal of Organic Chemistry
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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

Space GroupCrystallography714-bis(246-trimethylphenyl)-512-dibenzo[dd']s-indaceno[12-b:56-b']bisthiophene-551212-tetrone chloroform solvateCrystal SystemCrystal StructureCell ParametersExperimental 3D Coordinates
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CCDC 1949614: 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

{[1020-bis(246-trimethylphenyl)bisbenzo[45]indeno[12-b:1'2'-i]anthracene-818-diyl]bis(ethyne-21-diyl)}bis[tri-isopropylsilane]Space GroupCrystallographyCrystal SystemCrystal StructureCell ParametersExperimental 3D Coordinates
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CCDC 1949404: Experimental Crystal Structure Determination

2020

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

614-bis(4-t-butyl-26-dimethylphenyl)[1]benzothieno[2''3'':2'3']indeno[5'6':56]indeno[21-b][1]benzothiophene chloroform solvateSpace GroupCrystallographyCrystal SystemCrystal StructureCell ParametersExperimental 3D Coordinates
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CCDC 1949613: 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

Space GroupCrystallography{[919-bis(246-trimethylphenyl)bisbenzo[56]indeno[12-b:1'2'-i]anthracene-717-diyl]bis(ethyne-21-diyl)}bis[tri-isopropylsilane]Crystal SystemCrystal StructureCell ParametersExperimental 3D Coordinates
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CCDC 1994473: 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

614-bis(4-t-butyl-26-dimethylphenyl)-513-[1]benzothieno[2''3'':2'3']indeno[5'6':56]indeno[21-b][1]benzothiophene-551313-tetrone acetonitrile solvateSpace GroupCrystallographyCrystal SystemCrystal StructureCell ParametersExperimental 3D Coordinates
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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

Space GroupCrystallographyCrystal SystemCrystal StructureCell Parameters614-bis{[tri-isopropylsilyl]ethynyl}di-indeno[12-b:1'2'-i]anthracene-816-dioneExperimental 3D Coordinates
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CCDC 1949612: 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

Space GroupCrystallographyCrystal SystemCrystal Structure{[717-bis(246-trimethylphenyl)bisbenzo[67]indeno[12-b:1'2'-i]anthracene-919-diyl]bis(ethyne-21-diyl)}bis[tri-isopropylsilane] chloroform solvateCell ParametersExperimental 3D Coordinates
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CCDC 1589136: Experimental Crystal Structure Determination

2020

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

Space GroupCrystallography816-bis[246-tri-isopropylphenyl][1]benzothieno[3''2'':2'3']indeno[5'6':56]indeno[12-b][1]benzothiophene acetonitrile solvateCrystal SystemCrystal StructureCell ParametersExperimental 3D Coordinates
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CCDC 1995029: 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

Space GroupCrystallographyCrystal SystemCrystal StructureCell Parameters918-bis(4-t-butyl-26-dimethylphenyl)-514-[12]benzothiazino[4''3'':2'3']indeno[5'6':56]indeno[12-c][12]benzothiazine-551414-tetrone chloroform solvateExperimental 3D Coordinates
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CCDC 1964314: 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

{[918-bis(246-trimethylphenyl)[1]benzothieno[2'''3''':3''4'']cyclopenta[1''2'':6'7']naphtho[2'3':56]indeno[12-b][1]benzothiene-716-diyl]bis(ethyne-21-diyl)}bis[tri-isopropylsilane] chloroform solvateSpace GroupCrystallographyCrystal SystemCrystal StructureCell ParametersExperimental 3D Coordinates
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CCDC 1995030: 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

Space GroupCrystallographyCrystal System613-bis(4-t-butyl-26-dimethylphenyl)-512-dibenzo[dd']s-indaceno[21-b:65-b']bisthiophene-551212-tetrone chloroform dichloromethane acetonitrile solvateCrystal StructureCell ParametersExperimental 3D Coordinates
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