Substituted Cyclopentannulated Tetraazapentacenes.

cyclization dihydroazaacenes postfunctionalization semiconductors solid-state packing

Journal

Chemistry (Weinheim an der Bergstrasse, Germany)
ISSN: 1521-3765
Titre abrégé: Chemistry
Pays: Germany
ID NLM: 9513783

Informations de publication

Date de publication:
16 Nov 2022
Historique:
received: 14 06 2022
pubmed: 20 8 2022
medline: 20 8 2022
entrez: 19 8 2022
Statut: ppublish

Résumé

Brominated pentannulated dihydrotetraazapentacenes were prepared by gold- or palladium-catalyzed 5-endo-dig cyclization of TIPS-ethynylated dihydrotetraazaacenes (TIPS = triisopropylsilyl). Post-functionalization was demonstrated by Sonogashira alkynylation and Rosenmund-von Braun cyanation. Calculations predict these species to act as n-type semiconductors, which was verified for two derivates through characterization in organic field-effect transistors.

Identifiants

pubmed: 35983676
doi: 10.1002/chem.202201842
pmc: PMC9826220
doi:

Types de publication

Journal Article

Langues

eng

Sous-ensembles de citation

IM

Pagination

e202201842

Subventions

Organisme : Deutsche Forschungsgemeinschaft
ID : SFB1249

Informations de copyright

© 2022 The Authors. Chemistry - A European Journal published by Wiley-VCH GmbH.

Références

J Am Chem Soc. 2022 May 11;144(18):8306-8316
pubmed: 35471963
J Am Chem Soc. 2001 Sep 26;123(38):9482-3
pubmed: 11562247
Chem Rev. 2021 Jul 28;121(14):9113-9163
pubmed: 33315377
J Org Chem. 2013 Mar 15;78(6):2206-12
pubmed: 23323674
Angew Chem Int Ed Engl. 2018 Sep 17;57(38):12375-12379
pubmed: 30070417
Adv Mater. 2014 Aug 20;26(31):5541-9
pubmed: 24585514
Chem Commun (Camb). 2015 Feb 28;51(17):3604-7
pubmed: 25634022
J Am Chem Soc. 2020 Dec 2;142(48):20481-20488
pubmed: 33213145
Acc Chem Res. 2015 Jun 16;48(6):1676-86
pubmed: 25970089
European J Org Chem. 2017 Jan 3;2017(1):14-24
pubmed: 28747846
Chem Rev. 2007 Jul;107(7):3180-211
pubmed: 17580975
J Comput Chem. 2011 Nov 30;32(15):3218-25
pubmed: 21837726
J Org Chem. 2016 Feb 5;81(3):1198-205
pubmed: 26765520
Chem Commun (Camb). 2017 Jul 6;53(55):7772-7775
pubmed: 28650017
Chemistry. 2022 Nov 16;28(64):e202201842
pubmed: 35983676
Chemistry. 2021 Feb 15;27(10):3193-3212
pubmed: 33368683
Chemistry. 2021 Nov 25;27(66):16320-16324
pubmed: 34612544
Chemistry. 2015 Sep 21;21(39):13758-71
pubmed: 26248605
Chemistry. 2022 Feb 24;28(12):e202104203
pubmed: 35020239
Org Lett. 2010 May 7;12(9):2060-3
pubmed: 20373818
Chemistry. 2009 Jul 13;15(28):6780-9
pubmed: 19551789
Chemistry. 2021 Dec 1;27(67):16606-16610
pubmed: 34519387
Adv Mater. 2014 Nov 12;26(42):7190-6
pubmed: 25205623
Angew Chem Int Ed Engl. 2021 Apr 19;60(17):9270-9273
pubmed: 33259123
Angew Chem Int Ed Engl. 2015 May 11;54(20):6051-6
pubmed: 25820770
Org Lett. 2005 Jul 21;7(15):3163-6
pubmed: 16018611
Chemistry. 2007;13(17):4750-8
pubmed: 17373008
Acta Crystallogr B Struct Sci Cryst Eng Mater. 2020 Jun 1;76(Pt 3):427-435
pubmed: 32831261
Angew Chem Int Ed Engl. 2015 Dec 21;54(52):15762-6
pubmed: 26768696
Angew Chem Int Ed Engl. 2022 Jan 21;61(4):e202114277
pubmed: 34755928
Chem Rev. 2012 Apr 11;112(4):2208-67
pubmed: 22111507
Chemistry. 2017 May 23;23(29):7066-7073
pubmed: 28295719

Auteurs

Steffen Maier (S)

Organisch-Chemisches Institut (OCI), Heidelberg University, Im Neuenheimer Feld 270, 69120, Heidelberg, Germany.

Robin Heckershoff (R)

Organisch-Chemisches Institut (OCI), Heidelberg University, Im Neuenheimer Feld 270, 69120, Heidelberg, Germany.

Nikolai Hippchen (N)

Organisch-Chemisches Institut (OCI), Heidelberg University, Im Neuenheimer Feld 270, 69120, Heidelberg, Germany.

Kerstin Brödner (K)

Organisch-Chemisches Institut (OCI), Heidelberg University, Im Neuenheimer Feld 270, 69120, Heidelberg, Germany.

Frank Rominger (F)

Organisch-Chemisches Institut (OCI), Heidelberg University, Im Neuenheimer Feld 270, 69120, Heidelberg, Germany.

Jan Freudenberg (J)

Organisch-Chemisches Institut (OCI), Heidelberg University, Im Neuenheimer Feld 270, 69120, Heidelberg, Germany.

A Stephen K Hashmi (ASK)

Organisch-Chemisches Institut (OCI), Heidelberg University, Im Neuenheimer Feld 270, 69120, Heidelberg, Germany.
Chemistry Department, Faculty of Science, King Abdulaziz University, Jeddah, 21589, Saudi Arabia.

Uwe H F Bunz (UHF)

Organisch-Chemisches Institut (OCI), Heidelberg University, Im Neuenheimer Feld 270, 69120, Heidelberg, Germany.
Centre for Advanced Materials (CAM), Heidelberg University, Im Neuenheimer Feld 225, 69120, Heidelberg, Germany.

Classifications MeSH