Cyclobis(7,8‐(para‐quinodimethane)‐4,4′‐triphenylamine) and Its Cationic Species Showing Annulene‐Like Global (Anti)Aromaticity

π‐Conjugated macrocycles containing all‐benzenoid rings usually show local aromaticity, but reported herein is the macrocycle CBQT, containing alternating para‐quinodimethane and triphenylamine units displaying annulene‐like anti‐aromaticity at low temperatures as a result of structural rigidity and...

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Published inAngewandte Chemie International Edition Vol. 58; no. 34; pp. 11742 - 11746
Main Authors Dong, Shaoqiang, Gopalakrishna, Tullimilli Y., Han, Yi, Chi, Chunyan
Format Journal Article
LanguageEnglish
Published WEINHEIM Wiley 19.08.2019
Wiley Subscription Services, Inc
EditionInternational ed. in English
Subjects
Alkylation
annulenes
Aromaticity
Chemistry
Chemistry, Multidisciplinary
Conjugation
Crystal structure
Crystallography
Dehydrogenation
Low temperature
macrocycles
Nitrogen atoms
NMR
Nuclear magnetic resonance
Physical Sciences
porphyrinoids
radicals
Rigidity
Science & Technology
porphyrinoids
radicals
macrocycles
PI
annulenes
aromaticity
CHARACTERS
macrocycle, annulene, porphyrinoid, aromaticity, diradicaloid
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Abstract π‐Conjugated macrocycles containing all‐benzenoid rings usually show local aromaticity, but reported herein is the macrocycle CBQT, containing alternating para‐quinodimethane and triphenylamine units displaying annulene‐like anti‐aromaticity at low temperatures as a result of structural rigidity and participation of the bridging nitrogen atoms in π‐conjugation. It was easily synthesized by intermolecular Friedel–Crafts alkylation followed by oxidative dehydrogenation. X‐ray crystallographic structures of CBQT, as well as those of its dication, trication, and tetracation were obtained. The dication and tetracation exhibited global aromaticity and antiaromaticity, respectively, as confirmed by NMR measurements and theoretical calculations. Both the dication and tetracation possess open‐shell singlet ground states, with a small singlet–triplet gap. It's dynamic: The π‐conjugated macrocycle CBQT, containing alternating para‐quinodimethane and triphenylamine units, shows a temperature‐dependent dynamic process. It displays [32]annulene‐like antiaromaticity at low temperatures. Its dication and tetracation exhibit global aromaticity and anti‐aromaticity, respectively.
AbstractList π‐Conjugated macrocycles containing all‐benzenoid rings usually show local aromaticity, but reported herein is the macrocycle CBQT, containing alternating para‐quinodimethane and triphenylamine units displaying annulene‐like anti‐aromaticity at low temperatures as a result of structural rigidity and participation of the bridging nitrogen atoms in π‐conjugation. It was easily synthesized by intermolecular Friedel–Crafts alkylation followed by oxidative dehydrogenation. X‐ray crystallographic structures of CBQT, as well as those of its dication, trication, and tetracation were obtained. The dication and tetracation exhibited global aromaticity and antiaromaticity, respectively, as confirmed by NMR measurements and theoretical calculations. Both the dication and tetracation possess open‐shell singlet ground states, with a small singlet–triplet gap. It's dynamic: The π‐conjugated macrocycle CBQT, containing alternating para‐quinodimethane and triphenylamine units, shows a temperature‐dependent dynamic process. It displays [32]annulene‐like antiaromaticity at low temperatures. Its dication and tetracation exhibit global aromaticity and anti‐aromaticity, respectively.
π-Conjugated macrocycles containing all-benzenoid rings usually show local aromaticity, but reported herein is the macrocycle CBQT, containing alternating para-quinodimethane and triphenylamine units displaying annulene-like anti-aromaticity at low temperatures as a result of structural rigidity and participation of the bridging nitrogen atoms in π-conjugation. It was easily synthesized by intermolecular Friedel-Crafts alkylation followed by oxidative dehydrogenation. X-ray crystallographic structures of CBQT, as well as those of its dication, trication, and tetracation were obtained. The dication and tetracation exhibited global aromaticity and antiaromaticity, respectively, as confirmed by NMR measurements and theoretical calculations. Both the dication and tetracation possess open-shell singlet ground states, with a small singlet-triplet gap.π-Conjugated macrocycles containing all-benzenoid rings usually show local aromaticity, but reported herein is the macrocycle CBQT, containing alternating para-quinodimethane and triphenylamine units displaying annulene-like anti-aromaticity at low temperatures as a result of structural rigidity and participation of the bridging nitrogen atoms in π-conjugation. It was easily synthesized by intermolecular Friedel-Crafts alkylation followed by oxidative dehydrogenation. X-ray crystallographic structures of CBQT, as well as those of its dication, trication, and tetracation were obtained. The dication and tetracation exhibited global aromaticity and antiaromaticity, respectively, as confirmed by NMR measurements and theoretical calculations. Both the dication and tetracation possess open-shell singlet ground states, with a small singlet-triplet gap.
π‐Conjugated macrocycles containing all‐benzenoid rings usually show local aromaticity, but reported herein is the macrocycle CBQT, containing alternating para‐quinodimethane and triphenylamine units displaying annulene‐like anti‐aromaticity at low temperatures as a result of structural rigidity and participation of the bridging nitrogen atoms in π‐conjugation. It was easily synthesized by intermolecular Friedel–Crafts alkylation followed by oxidative dehydrogenation. X‐ray crystallographic structures of CBQT, as well as those of its dication, trication, and tetracation were obtained. The dication and tetracation exhibited global aromaticity and antiaromaticity, respectively, as confirmed by NMR measurements and theoretical calculations. Both the dication and tetracation possess open‐shell singlet ground states, with a small singlet–triplet gap.
π‐Conjugated macrocycles containing all‐benzenoid rings usually show local aromaticity, but reported herein is the macrocycle CBQT , containing alternating para ‐quinodimethane and triphenylamine units displaying annulene‐like anti‐aromaticity at low temperatures as a result of structural rigidity and participation of the bridging nitrogen atoms in π‐conjugation. It was easily synthesized by intermolecular Friedel–Crafts alkylation followed by oxidative dehydrogenation. X‐ray crystallographic structures of CBQT , as well as those of its dication, trication, and tetracation were obtained. The dication and tetracation exhibited global aromaticity and antiaromaticity, respectively, as confirmed by NMR measurements and theoretical calculations. Both the dication and tetracation possess open‐shell singlet ground states, with a small singlet–triplet gap.
pi-Conjugated macrocycles containing all-benzenoid rings usually show local aromaticity, but reported herein is the macrocycle CBQT, containing alternating para-quinodimethane and triphenylamine units displaying annulene-like anti-aromaticity at low temperatures as a result of structural rigidity and participation of the bridging nitrogen atoms in pi-conjugation. It was easily synthesized by intermolecular Friedel-Crafts alkylation followed by oxidative dehydrogenation. X-ray crystallographic structures of CBQT, as well as those of its dication, trication, and tetracation were obtained. The dication and tetracation exhibited global aromaticity and antiaromaticity, respectively, as confirmed by NMR measurements and theoretical calculations. Both the dication and tetracation possess open-shell singlet ground states, with a small singlet-triplet gap.
π-Conjugated macrocycles containing all-benzenoid rings usually show local aromaticity, but herein we report that a macrocycle (CBQT) containing alternating para-quinodimethane and triphenylamine units displayed annulene-like anti-aromaticity at low temperatures due to structural rigidity and participation in π-conjugation of the bridging nitrogen atoms. It was facilely synthesized by intermolecular Friedel-Crafts alkylation followed by oxidative dehydrogenation. X-ray crystallographic structures of CBQT as well as its dication, trication and tetracation were obtained. The dication and tetracation exhibited global aromaticity and antiaromaticity, respectively, as confirmed by NMR measurements and theoretic calculations. Both the dication and tetracation possess open-shell singlet ground state, with a small singlet-triplet gap.
Author Han, Yi
Gopalakrishna, Tullimilli Y.
Chi, Chunyan
Dong, Shaoqiang
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  fullname: Gopalakrishna, Tullimilli Y.
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  orcidid: 0000-0003-4677-3546
  surname: Chi
  fullname: Chi, Chunyan
  email: chmcc@nus.edu.sg
  organization: National University of Singapore
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Keywords porphyrinoids
radicals
macrocycles
PI
annulenes
aromaticity
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macrocycle, annulene, porphyrinoid, aromaticity, diradicaloid
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Snippet π‐Conjugated macrocycles containing all‐benzenoid rings usually show local aromaticity, but reported herein is the macrocycle CBQT, containing alternating...
π‐Conjugated macrocycles containing all‐benzenoid rings usually show local aromaticity, but reported herein is the macrocycle CBQT , containing alternating...
pi-Conjugated macrocycles containing all-benzenoid rings usually show local aromaticity, but reported herein is the macrocycle CBQT, containing alternating...
π-Conjugated macrocycles containing all-benzenoid rings usually show local aromaticity, but herein we report that a macrocycle (CBQT) containing alternating...
π-Conjugated macrocycles containing all-benzenoid rings usually show local aromaticity, but reported herein is the macrocycle CBQT, containing alternating...
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StartPage 11742
SubjectTerms Alkylation
annulenes
Aromaticity
Chemistry
Chemistry, Multidisciplinary
Conjugation
Crystal structure
Crystallography
Dehydrogenation
Low temperature
macrocycles
Nitrogen atoms
NMR
Nuclear magnetic resonance
Physical Sciences
porphyrinoids
radicals
Rigidity
Science & Technology
Title Cyclobis(7,8‐(para‐quinodimethane)‐4,4′‐triphenylamine) and Its Cationic Species Showing Annulene‐Like Global (Anti)Aromaticity
URI https://onlinelibrary.wiley.com/doi/abs/10.1002%2Fanie.201905763
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https://www.ncbi.nlm.nih.gov/pubmed/31225671
https://www.proquest.com/docview/2269868694
https://www.proquest.com/docview/2245643193
Volume 58
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