title: Diazatetracenes Derived from the Benzannulation of Acetylenes: Electronic Tuning via Substituent Effects and External Stimuli.
abstract: Functionalized diazatetracenes are prepared using a new two-step sequence. The use of a dichlorobenzaldehyde in a Cu-catalyzed benzannulation of acetylenes provides functionalized dichloronaphthalenes that afford diazatetracenes using Buchwald-Hartwig aminations. This approach provides unique substitution patterns and rapid access to covalently linked dimeric diazatetracenes. Their electronic properties are characterized by UV-vis absorption/emission and cyclic voltammetry, revealing strong effects from both external stimuli by acid and internal substituent effects.
authors.affiliation: Department of Chemistry and Chemical Biology, Baker Laboratory, Cornell University , Ithaca, New York 14853, United States.
authors.forename: Dan
authors.identifier: 0000-0001-8392-1208
authors.initials: D
authors.lastname: Lehnherr
authors.affiliation: Department of Chemistry and Chemical Biology, Baker Laboratory, Cornell University , Ithaca, New York 14853, United States.|Department of Chemistry, Northwestern University , Evanston, Illinois 60208, United States.
authors.forename: Joaquin M
authors.initials: JM
authors.lastname: Alzola
authors.affiliation: Department of Chemistry and Chemical Biology, Baker Laboratory, Cornell University , Ithaca, New York 14853, United States.
authors.forename: Catherine R
authors.identifier: 0000-0002-4013-4025
authors.initials: CR
authors.lastname: Mulzer
authors.affiliation: Department of Chemistry and Chemical Biology, Baker Laboratory, Cornell University , Ithaca, New York 14853, United States.|Department of Chemistry, Northwestern University , Evanston, Illinois 60208, United States.
authors.forename: Samuel J
authors.initials: SJ
authors.lastname: Hein
authors.affiliation: Department of Chemistry and Chemical Biology, Baker Laboratory, Cornell University , Ithaca, New York 14853, United States.|Department of Chemistry, Northwestern University , Evanston, Illinois 60208, United States.
authors.forename: William R
authors.identifier: 0000-0002-3635-6119
authors.initials: WR
authors.lastname: Dichtel