Modulating the Electronic and Solid-State Structure of Organic Semiconductors by Site-Specific Substitution: The Case of Tetrafluoropentacenes.
acenes
organic field-effect transistors
organic semiconductors
singlet fission
synthesis
Journal
Chemistry (Weinheim an der Bergstrasse, Germany)
ISSN: 1521-3765
Titre abrégé: Chemistry
Pays: Germany
ID NLM: 9513783
Informations de publication
Date de publication:
12 Mar 2020
12 Mar 2020
Historique:
received:
27
12
2019
pubmed:
28
1
2020
medline:
28
1
2020
entrez:
28
1
2020
Statut:
ppublish
Résumé
The properties as well as solid-state structures, singlet fission, and organic field-effect transistor (OFET) performance of three tetrafluoropentacenes (1,4,8,11: 10, 1,4,9,10: 11, 2,3,9,10: 12) are compared herein. The novel compounds 10 and 11 were synthesized in high purity from the corresponding 6,13-etheno-bridged precursors by reaction with dimethyl 1,2,4,5-tetrazine-3,6-dicarboxylate at elevated temperatures. Although most of the molecular properties of the compounds are similar, their chemical reactivity and crystal structures differ considerably. Isomer 10 undergoes the orbital symmetry forbidden thermal [4+4] dimerization, whereas 11 and 12 are much less reactive. The isomers 11 and 12 crystallize in a herringbone motif, but 10 prefers π-π stacking. Although the energy of the first electric dipole-allowed optical transition varies only within 370 cm
Identifiants
pubmed: 31985891
doi: 10.1002/chem.201905843
pmc: PMC7154741
doi:
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
3420-3434Subventions
Organisme : Deutsche Forschungsgemeinschaft
ID : INST 40/467-1
Informations de copyright
© 2020 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA.
Références
Phys Chem Chem Phys. 2018 Feb 21;20(8):5795-5802
pubmed: 29411801
Chem Soc Rev. 2005 Jan;34(1):22-30
pubmed: 15643487
J Phys Chem Lett. 2016 Jul 7;7(13):2370-5
pubmed: 27281713
ACS Appl Mater Interfaces. 2015 Sep 9;7(35):19774-80
pubmed: 26287576
J Am Chem Soc. 2019 Jun 5;141(22):8834-8845
pubmed: 31063690
Chemistry. 2020 Mar 12;26(15):3420-3434
pubmed: 31985891
J Org Chem. 2019 Aug 16;84(16):10120-10135
pubmed: 31390211
Chem Rev. 2010 Nov 10;110(11):6891-936
pubmed: 21053979
Angew Chem Int Ed Engl. 2008;47(3):452-83
pubmed: 18046697
J Phys Chem Lett. 2014 Oct 2;5(19):3345-53
pubmed: 26278443
Org Lett. 2005 Jul 21;7(15):3163-6
pubmed: 16018611
Phys Chem Chem Phys. 2018 Dec 12;20(48):30083-30094
pubmed: 30484452
J Am Chem Soc. 2017 Mar 29;139(12):4435-4442
pubmed: 28319405
J Phys Chem Lett. 2013 Apr 4;4(7):1065-9
pubmed: 26282022
Chem Rev. 2006 Dec;106(12):5028-48
pubmed: 17165682
J Chem Phys. 2019 Oct 28;151(16):164706
pubmed: 31675857
J Am Chem Soc. 2007 Aug 29;129(34):10316-7
pubmed: 17672461
Adv Mater. 2013 Jan 18;25(3):313-30
pubmed: 22865814
Chem Asian J. 2009 Feb 2;4(2):294-301
pubmed: 19072938
J Am Chem Soc. 2015 Jun 3;137(21):6790-803
pubmed: 25946670
Sci Technol Adv Mater. 2009 Jul 6;10(2):024313
pubmed: 27877286
J Org Chem. 2016 Aug 5;81(15):6223-34
pubmed: 27362625
Nat Commun. 2012;3:1259
pubmed: 23232389
J Am Chem Soc. 2011 Aug 10;133(31):11830-3
pubmed: 21755937
Science. 2011 Dec 16;334(6062):1541-5
pubmed: 22174249
J Org Chem. 2018 Mar 16;83(6):3149-3158
pubmed: 29485868
J Org Chem. 2012 Apr 6;77(7):3538-42
pubmed: 22443182
J Org Chem. 2001 Aug 10;66(16):5517-21
pubmed: 11485476
J Am Chem Soc. 2009 Apr 15;131(14):5264-73
pubmed: 19317404
J Am Chem Soc. 2004 Jul 7;126(26):8138-40
pubmed: 15225054
Chemphyschem. 2006 Sep 11;7(9):2003-7
pubmed: 16952119
Chemphyschem. 2015 Apr 27;16(6):1251-7
pubmed: 25640856
Chemistry. 2012 Feb 6;18(6):1789-99
pubmed: 22213393
ACS Nano. 2014 Jul 22;8(7):7377-83
pubmed: 24957197
J Am Chem Soc. 2008 May 14;130(19):6064-5
pubmed: 18412338
Chem Rev. 2019 Mar 27;119(6):4261-4292
pubmed: 30721032
J Am Chem Soc. 2008 Jun 11;130(23):7300-4
pubmed: 18479108
J Am Chem Soc. 2014 Nov 5;136(44):15798-805
pubmed: 25303232
J Am Chem Soc. 2019 Apr 17;141(15):6191-6203
pubmed: 30854854
J Am Chem Soc. 2011 Jul 20;133(28):10803-16
pubmed: 21710966
Chemphyschem. 2008 Aug 4;9(11):1519-23
pubmed: 18537216