0000000001299529

AUTHOR

R. Graeme Soper

showing 9 related works from this author

Mono‐ and Bis(imidazolidinium ethynyl) Cations and Reduction of the Latter To Give an Extended Bis‐1,4‐([3]Cumulene)‐p-carboquinoid System

2017

An extended π-system containing two [3]cumulene fragments separated by a p-carboquinoid and stabilized by two capping N-heterocyclic carbenes (NHCs) has been prepared. Mono- and bis(imidazolidinium ethynyl) cations have also been synthesized from the reaction of an NHC with phenylethynyl bromide or 1,4-bis(bromoethynyl)benzene. Cyclic voltammetry coupled with synthetic and structural studies showed that the dication is readily reduced to a neutral, singlet bis-1,4-([3]cumulene)-p-carboquinoid as a result of the π-accepting properties of the capping NHCs. peerReviewed

cumulenes010405 organic chemistryreductionGeneral MedicineN-heterocyclic carbenes010402 general chemistryalkynes01 natural sciencespropargyl cations0104 chemical sciences3. Good health
researchProduct

Mono‐ and Bis(imidazolidinium ethynyl) Cations and Reduction of the Latter To Give an Extended Bis‐1,4‐([3]Cumulene)‐ p ‐carboquinoid System

2018

An extended π-system containing two [3]cumulene fragments separated by a p-carboquinoid and stabilized by two capping N-heterocyclic carbenes (NHCs) has been prepared. Mono- and bis(imidazolidinium ethynyl) cations have also been synthesized from the reaction of an NHC with phenylethynyl bromide or 1,4-bis(bromoethynyl)benzene. Cyclic voltammetry coupled with synthetic and structural studies showed that the dication is readily reduced to a neutral, singlet bis-1,4-([3]cumulene)-p-carboquinoid as a result of the π-accepting properties of the capping NHCs.

010405 organic chemistryCumuleneGeneral Chemistry010402 general chemistryPhotochemistry01 natural sciencesMedicinal chemistryCatalysis0104 chemical sciences3. Good healthDicationchemistry.chemical_compoundchemistryBromideX-ray crystallographySinglet stateCyclic voltammetryBenzeneAngewandte Chemie International Edition
researchProduct

CCDC 1549500: Experimental Crystal Structure Determination

2017

Related Article: Brian M. Barry, R. Graeme Soper, Juha Hurmalainen, Akseli Mansikkamäki, Katherine N. Robertson, William L. McClennan, Alex J. Veinot, Tracey L. Roemmele, Ulrike Werner-Zwanziger, René T. Boeré, Heikki M. Tuononen, Jason A. C. Clyburne, Jason D. Masuda|2018|Angew.Chem.,Int.Ed.|57|749|doi:10.1002/anie.201711031

2-{[4-(chloroethynyl)phenyl]ethynyl}-13-bis[26-bis(propan-2-yl)phenyl]-45-dihydro-1H-imidazol-3-ium 2-{[4-(bromoethynyl)phenyl]ethynyl}-13-bis[26-bis(propan-2-yl)phenyl]-45-dihydro-1H-imidazol-3-ium tetraphenylborate dichloromethane solvateSpace GroupCrystallographyCrystal SystemCrystal StructureCell ParametersExperimental 3D Coordinates
researchProduct

CCDC 1549501: Experimental Crystal Structure Determination

2017

Related Article: Brian M. Barry, R. Graeme Soper, Juha Hurmalainen, Akseli Mansikkamäki, Katherine N. Robertson, William L. McClennan, Alex J. Veinot, Tracey L. Roemmele, Ulrike Werner-Zwanziger, René T. Boeré, Heikki M. Tuononen, Jason A. C. Clyburne, Jason D. Masuda|2018|Angew.Chem.,Int.Ed.|57|749|doi:10.1002/anie.201711031

Space GroupCrystallographyCrystal SystemCrystal StructureCell Parameters22'-[cyclohexa-25-diene-14-diylidenebis(ethene-21-diylidene)]bis{13-bis[26-bis(propan-2-yl)phenyl]imidazolidine}Experimental 3D Coordinates
researchProduct

CCDC 1549502: Experimental Crystal Structure Determination

2017

Related Article: Brian M. Barry, R. Graeme Soper, Juha Hurmalainen, Akseli Mansikkamäki, Katherine N. Robertson, William L. McClennan, Alex J. Veinot, Tracey L. Roemmele, Ulrike Werner-Zwanziger, René T. Boeré, Heikki M. Tuononen, Jason A. C. Clyburne, Jason D. Masuda|2018|Angew.Chem.,Int.Ed.|57|749|doi:10.1002/anie.201711031

Space GroupCrystallographyCrystal SystemCrystal StructureCell Parameters13-bis[26-bis(propan-2-yl)phenyl]-2-(phenylethynyl)-45-dihydro-1H-imidazol-3-ium hexafluorophosphate dichloromethane solvateExperimental 3D Coordinates
researchProduct

CCDC 1549499: Experimental Crystal Structure Determination

2017

Related Article: Brian M. Barry, R. Graeme Soper, Juha Hurmalainen, Akseli Mansikkamäki, Katherine N. Robertson, William L. McClennan, Alex J. Veinot, Tracey L. Roemmele, Ulrike Werner-Zwanziger, René T. Boeré, Heikki M. Tuononen, Jason A. C. Clyburne, Jason D. Masuda|2018|Angew.Chem.,Int.Ed.|57|749|doi:10.1002/anie.201711031

Space GroupCrystallographyCrystal System22'-(14-phenylenedi(ethyne-21-diyl))bis(13-bis[26-di(propan-2-yl)phenyl]-45-dihydro-1H-imidazol-3-ium) bis(bromide) dichloromethane solvate dihydrateCrystal StructureCell ParametersExperimental 3D Coordinates
researchProduct

CCDC 1549503: Experimental Crystal Structure Determination

2017

Related Article: Brian M. Barry, R. Graeme Soper, Juha Hurmalainen, Akseli Mansikkamäki, Katherine N. Robertson, William L. McClennan, Alex J. Veinot, Tracey L. Roemmele, Ulrike Werner-Zwanziger, René T. Boeré, Heikki M. Tuononen, Jason A. C. Clyburne, Jason D. Masuda|2018|Angew.Chem.,Int.Ed.|57|749|doi:10.1002/anie.201711031

Space GroupCrystallography13-bis[26-bis(propan-2-yl)phenyl]-2-[(4-fluorophenyl)ethynyl]-45-dihydro-1H-imidazol-3-ium hexafluorophosphate dichloromethane solvateCrystal SystemCrystal StructureCell ParametersExperimental 3D Coordinates
researchProduct

CCDC 1549498: Experimental Crystal Structure Determination

2017

Related Article: Brian M. Barry, R. Graeme Soper, Juha Hurmalainen, Akseli Mansikkamäki, Katherine N. Robertson, William L. McClennan, Alex J. Veinot, Tracey L. Roemmele, Ulrike Werner-Zwanziger, René T. Boeré, Heikki M. Tuononen, Jason A. C. Clyburne, Jason D. Masuda|2018|Angew.Chem.,Int.Ed.|57|749|doi:10.1002/anie.201711031

Space GroupCrystallographyCrystal System13-bis[26-bis(propan-2-yl)phenyl]-2-(phenylethynyl)-45-dihydro-1H-imidazol-3-ium bromide toluene solvateCrystal StructureCell ParametersExperimental 3D Coordinates
researchProduct

CCDC 1549504: Experimental Crystal Structure Determination

2017

Related Article: Brian M. Barry, R. Graeme Soper, Juha Hurmalainen, Akseli Mansikkamäki, Katherine N. Robertson, William L. McClennan, Alex J. Veinot, Tracey L. Roemmele, Ulrike Werner-Zwanziger, René T. Boeré, Heikki M. Tuononen, Jason A. C. Clyburne, Jason D. Masuda|2018|Angew.Chem.,Int.Ed.|57|749|doi:10.1002/anie.201711031

Space GroupCrystallographyCrystal SystemCrystal Structure2-[([11'-biphenyl]-4-yl)ethynyl]-13-bis[26-bis(propan-2-yl)phenyl]-45-dihydro-1H-imidazol-3-ium bromide dichloromethane solvateCell ParametersExperimental 3D Coordinates
researchProduct