Azaarenes: 13 Rings in a Row by Cyclopentannulation.

Aromaticity Azaacenes Azaarenes Cyclopentannulation Molecular Nanocarbons

Journal

Angewandte Chemie (International ed. in English)
ISSN: 1521-3773
Titre abrégé: Angew Chem Int Ed Engl
Pays: Germany
ID NLM: 0370543

Informations de publication

Date de publication:
26 Jan 2023
Historique:
received: 22 09 2022
pubmed: 17 11 2022
medline: 17 11 2022
entrez: 16 11 2022
Statut: ppublish

Résumé

Cyclopentannulation was explored as a strategy to access large, stable azaarenes. Buchwald-Hartwig coupling of previously reported di- and tetrabrominated cyclopentannulated N,N'-dihydrotetraazapentacenes furnished stable azaarenes with up to 13 six-membered rings in a row and a length of 3.1 nm. Their optoelectronic and semi-conducting properties as well as their aromaticity were investigated.

Identifiants

pubmed: 36383088
doi: 10.1002/anie.202214031
pmc: PMC10107455
doi:

Types de publication

Journal Article

Langues

eng

Sous-ensembles de citation

IM

Pagination

e202214031

Subventions

Organisme : Deutsche Forschungsgesellschaft
ID : SFB1249
Organisme : Deutsche Forschungsgesellschaft
ID : INST 40/575-1 FUGG
Organisme : State of Baden-Württemberg

Informations de copyright

© 2022 The Authors. Angewandte Chemie International Edition published by Wiley-VCH GmbH.

Références

Angew Chem Int Ed Engl. 2020 Dec 21;59(52):23386-23401
pubmed: 32720441
Adv Mater. 2014 Nov 12;26(42):7190-6
pubmed: 25205623
J Phys Chem B. 2009 Jul 2;113(26):8813-9
pubmed: 19552453
Angew Chem Int Ed Engl. 2020 Jan 13;59(3):1113-1117
pubmed: 31647593
Angew Chem Int Ed Engl. 2011 Jul 25;50(31):7013-7
pubmed: 21717552
Org Lett. 2011 Oct 21;13(20):5692-5
pubmed: 21942870
Chem Commun (Camb). 2017 Jul 6;53(55):7772-7775
pubmed: 28650017
Chemistry. 2018 Jun 7;24(32):8087-8091
pubmed: 29658160
Chemistry. 2019 Aug 22;25(47):11121-11134
pubmed: 31210369
Chemistry. 2016 Mar 24;22(14):4680-9
pubmed: 26889601
Chemistry. 2022 Nov 16;28(64):e202201842
pubmed: 35983676
Angew Chem Int Ed Engl. 2020 Jan 27;59(5):1966-1969
pubmed: 31724294
Chemistry. 2018 Sep 3;24(49):12801-12805
pubmed: 29964330
Org Lett. 2016 Sep 16;18(18):4694-7
pubmed: 27602601
Nat Commun. 2022 Jan 11;13(1):223
pubmed: 35017480
Chem Commun (Camb). 2011 Jan 7;47(1):514-6
pubmed: 20972504
Chem Soc Rev. 2014 Sep 7;43(17):6311-24
pubmed: 24841033
Chem Commun (Camb). 2014 Feb 25;50(16):1976-9
pubmed: 24406939
Chemistry. 2017 Oct 12;23(57):14101-14112
pubmed: 28810077
J Am Chem Soc. 2016 Jul 27;138(29):9137-44
pubmed: 27352727
Chemistry. 2014 Aug 18;20(34):10626-31
pubmed: 24677280
Angew Chem Int Ed Engl. 2018 Sep 17;57(38):12375-12379
pubmed: 30070417
Chemistry. 2018 Jan 24;24(5):1036-1040
pubmed: 28976041
Phys Chem Chem Phys. 2016 Apr 28;18(17):11616-9
pubmed: 26910505
Chemistry. 2021 Feb 15;27(10):3193-3212
pubmed: 33368683
Org Lett. 2013 Jul 19;15(14):3594-7
pubmed: 23822170
Chem Rev. 2005 Oct;105(10):3758-72
pubmed: 16218566
Angew Chem Int Ed Engl. 2021 Jul 12;60(29):16230-16236
pubmed: 33999484
Org Lett. 2012 Aug 17;14(16):4170-3
pubmed: 22866987
Acc Chem Res. 2019 Sep 17;52(9):2491-2505
pubmed: 31478641
Angew Chem Int Ed Engl. 2016 Aug 22;55(35):10427-30
pubmed: 27457893
ACS Nano. 2020 Jan 28;14(1):1011-1017
pubmed: 31829618
Angew Chem Int Ed Engl. 2021 Mar 29;60(14):7941-7946
pubmed: 33460231
Org Lett. 2012 Jan 20;14(2):494-7
pubmed: 22216998
Chemistry. 2020 Sep 4;26(50):11634-11642
pubmed: 32459010
J Am Chem Soc. 2016 Feb 17;138(6):1792-5
pubmed: 26808212
J Am Chem Soc. 2022 Jun 8;144(22):9883-9892
pubmed: 35635258
Chem Rec. 2016 Jun;16(3):1518-30
pubmed: 27219103
Chem Sci. 2020 Sep 16;11(41):11235-11243
pubmed: 34094364
Chem Commun (Camb). 2015 Feb 28;51(17):3604-7
pubmed: 25634022
Angew Chem Int Ed Engl. 2022 Jul 4;61(27):e202205018
pubmed: 35467070
Chem Rev. 2000 Apr 12;100(4):1605-44
pubmed: 11749277
Acc Chem Res. 2019 Oct 15;52(10):2757-2759
pubmed: 31610660
Nat Commun. 2011 Aug 16;2:437
pubmed: 21847111
Chemistry. 2016 Oct 10;22(42):14840-14845
pubmed: 27428573
Org Lett. 2015 Dec 4;17(23):5902-5
pubmed: 26588192
J Am Chem Soc. 2021 May 5;143(17):6593-6600
pubmed: 33876941
Chem Soc Rev. 2015 Sep 21;44(18):6616-43
pubmed: 26186682
Angew Chem Int Ed Engl. 2008;47(3):452-83
pubmed: 18046697
Angew Chem Int Ed Engl. 2018 Jan 15;57(3):703-708
pubmed: 29193535
Adv Mater. 2018 Sep;30(38):e1803467
pubmed: 30066472
Angew Chem Int Ed Engl. 2016 Dec 12;55(50):15594-15598
pubmed: 27649907
Angew Chem Int Ed Engl. 2015 May 11;54(20):6051-6
pubmed: 25820770
J Am Chem Soc. 2008 Jul 2;130(26):8297-306
pubmed: 18540576
Chem Asian J. 2016 Feb 18;11(4):482-5
pubmed: 26603787
J Am Chem Soc. 2019 Apr 3;141(13):5130-5134
pubmed: 30860825
Angew Chem Int Ed Engl. 2015 Dec 21;54(52):15762-6
pubmed: 26768696
Angew Chem Int Ed Engl. 2008;47(34):6338-61
pubmed: 18663711
Acta Crystallogr B Struct Sci Cryst Eng Mater. 2020 Jun 1;76(Pt 3):427-435
pubmed: 32831261
Chemistry. 2009;15(20):4990-3
pubmed: 19338039
J Am Chem Soc. 2016 Aug 17;138(32):10323-30
pubmed: 27435865
Nano Lett. 2020 Jul 8;20(7):4718-4720
pubmed: 32510230
Org Lett. 2017 Apr 7;19(7):1718-1721
pubmed: 28291368
Chem Commun (Camb). 2020 Sep 29;56(77):11457-11460
pubmed: 32852499
Angew Chem Int Ed Engl. 2022 Nov 2;61(44):e202209286
pubmed: 35822738
J Am Chem Soc. 2022 Jul 6;144(26):11499-11524
pubmed: 35671225
J Am Chem Soc. 2017 Sep 20;139(37):13102-13109
pubmed: 28829125
Chemistry. 2014 May 5;20(19):5673-88
pubmed: 24677667
Chem Asian J. 2010 Mar 1;5(3):482-5
pubmed: 19998440
Org Biomol Chem. 2013 Oct 7;11(37):6285-91
pubmed: 23942821
Angew Chem Int Ed Engl. 2023 Jan 26;62(5):e202214031
pubmed: 36383088

Auteurs

Steffen Maier (S)

Organisch-Chemisches Institut, Ruprecht-Karls-Universität Heidelberg, Im Neuenheimer Feld 270, 69120, Heidelberg, Germany.

Nikolai Hippchen (N)

Organisch-Chemisches Institut, Ruprecht-Karls-Universität Heidelberg, Im Neuenheimer Feld 270, 69120, Heidelberg, Germany.

Fabian Jester (F)

Organisch-Chemisches Institut, Ruprecht-Karls-Universität Heidelberg, Im Neuenheimer Feld 270, 69120, Heidelberg, Germany.

Marcus Dodds (M)

Organisch-Chemisches Institut, Ruprecht-Karls-Universität Heidelberg, Im Neuenheimer Feld 270, 69120, Heidelberg, Germany.

Michel Weber (M)

Organisch-Chemisches Institut, Ruprecht-Karls-Universität Heidelberg, Im Neuenheimer Feld 270, 69120, Heidelberg, Germany.

Leon Skarjan (L)

Organisch-Chemisches Institut, Ruprecht-Karls-Universität Heidelberg, Im Neuenheimer Feld 270, 69120, Heidelberg, Germany.

Frank Rominger (F)

Organisch-Chemisches Institut, Ruprecht-Karls-Universität Heidelberg, Im Neuenheimer Feld 270, 69120, Heidelberg, Germany.

Jan Freudenberg (J)

Organisch-Chemisches Institut, Ruprecht-Karls-Universität Heidelberg, Im Neuenheimer Feld 270, 69120, Heidelberg, Germany.

Uwe H F Bunz (UHF)

Organisch-Chemisches Institut, Ruprecht-Karls-Universität Heidelberg, Im Neuenheimer Feld 270, 69120, Heidelberg, Germany.
Centre for Advanced Materials, Ruprecht-Karls-Universität Heidelberg, Im Neuenheimer Feld 225, 69120, Heidelberg, Germany.

Classifications MeSH