Synthesis and Characterizations of 5,5'-Bibenzo[rst]pentaphene with Axial Chirality and Symmetry-Breaking Charge Transfer.
axial chirality
benzo[rst]pentaphene
biaryl
symmetry-breaking charge transfer
transient absorption
Journal
Advanced science (Weinheim, Baden-Wurttemberg, Germany)
ISSN: 2198-3844
Titre abrégé: Adv Sci (Weinh)
Pays: Germany
ID NLM: 101664569
Informations de publication
Date de publication:
07 2022
07 2022
Historique:
revised:
23
01
2022
received:
01
01
2022
pubmed:
15
2
2022
medline:
9
7
2022
entrez:
14
2
2022
Statut:
ppublish
Résumé
Exploration of novel biaryls consisting of two polycyclic aromatic hydrocarbon (PAH) units can be an important strategy toward further developments of organic materials with unique properties. In this study, 5,5'-bibenzo[rst]pentaphene (BBPP) with two benzo[rst]pentaphene (BPP) units is synthesized in an efficient and versatile approach, and its structure is unambiguously elucidated by X-ray crystallography. BBPP exhibits axial chirality, and the (M)- and (P)-enantiomers are resolved by chiral high-performance liquid chromatography and studied by circular dichroism spectroscopy. These enantiomers have a relatively high isomerization barrier of 43.6 kcal mol
Identifiants
pubmed: 35156332
doi: 10.1002/advs.202200004
pmc: PMC9259715
doi:
Substances chimiques
Polycyclic Aromatic Hydrocarbons
0
Solvents
0
Types de publication
Journal Article
Research Support, Non-U.S. Gov't
Research Support, U.S. Gov't, P.H.S.
Langues
eng
Sous-ensembles de citation
IM
Pagination
e2200004Subventions
Organisme : Max Planck Society
Organisme : Okinawa Institute of Science and Technology Graduate University
Organisme : University of Bologna
Organisme : JSPS
ID : JP19K24686
Organisme : Institute for Chemical Research, Kyoto University
ID : 2019-40
Organisme : Institute for Chemical Research, Kyoto University
ID : 2020-38
Organisme : Kavli Institute at Cornell
Organisme : American Society for Engineering Education
Organisme : National Science Foundation
ID : #EEC-2127509
Informations de copyright
© 2022 The Authors. Advanced Science published by Wiley-VCH GmbH.
Références
Chemphyschem. 2012 Jun 4;13(8):2001-11
pubmed: 22473631
Chem Soc Rev. 2013 Aug 21;42(16):6990-7027
pubmed: 23783506
J Chem Phys. 2009 Dec 14;131(22):224315
pubmed: 20001044
Adv Sci (Weinh). 2022 Jul;9(19):e2200004
pubmed: 35156332
J Am Chem Soc. 2004 Apr 14;126(14):4641-5
pubmed: 15070380
J Am Chem Soc. 2008 Mar 26;130(12):3788-96
pubmed: 18314972
Org Lett. 2021 Feb 19;23(4):1349-1354
pubmed: 33533627
J Phys Chem Lett. 2019 Jun 20;10(12):3481-3487
pubmed: 31081636
Chem Commun (Camb). 2018 Jun 19;54(50):6705-6718
pubmed: 29799051
J Org Chem. 2000 Jun 30;65(13):3952-60
pubmed: 10866613
Angew Chem Int Ed Engl. 2018 Nov 26;57(48):15862-15865
pubmed: 30395384
Acc Chem Res. 2019 Jul 16;52(7):1812-1823
pubmed: 31264834
J Am Chem Soc. 2015 Apr 22;137(15):5130-9
pubmed: 25825939
Chem Commun (Camb). 2012 Jan 7;48(2):284-6
pubmed: 22105418
Chem Rev. 2003 Oct;103(10):3899-4032
pubmed: 14531716
Acc Chem Res. 2019 Sep 17;52(9):2472-2481
pubmed: 31411855
J Am Chem Soc. 2016 Apr 6;138(13):4643-9
pubmed: 26986957
J Am Chem Soc. 2011 Nov 2;133(43):17262-73
pubmed: 21939246
Chem Soc Rev. 2021 Mar 7;50(5):2968-2983
pubmed: 33491680
J Am Chem Soc. 2016 Mar 30;138(12):3990-3
pubmed: 26967372
Acc Chem Res. 2007 Dec;40(12):1385-93
pubmed: 17685581
J Am Chem Soc. 2019 Dec 26;141(51):19994-19999
pubmed: 31816238
Nat Commun. 2018 Nov 12;9(1):4756
pubmed: 30420660
J Am Chem Soc. 2013 Aug 28;135(34):12747-54
pubmed: 23883167
J Am Chem Soc. 2005 Mar 30;127(12):4286-96
pubmed: 15783210
Angew Chem Int Ed Engl. 2011 Aug 8;50(33):7596-8
pubmed: 21728220
J Phys Chem B. 2010 Jul 8;114(26):8585-92
pubmed: 20552975
Chemistry. 2007;13(26):7349-57
pubmed: 17579898
J Am Chem Soc. 2002 Jul 24;124(29):8530-1
pubmed: 12121085
J Phys Chem Lett. 2019 Apr 18;10(8):1919-1927
pubmed: 30892901
Org Lett. 2016 May 6;18(9):2118-21
pubmed: 27120727
Angew Chem Int Ed Engl. 2020 May 25;59(22):8571-8578
pubmed: 32220117
Chem Rev. 2017 Feb 22;117(4):3479-3716
pubmed: 27258218
Annu Rev Phys Chem. 2019 Jun 14;70:323-351
pubmed: 31174458
Chirality. 2008 Mar;20(3-4):295-300
pubmed: 17597115
J Mol Model. 2019 Jun 7;25(7):183
pubmed: 31175477
Chem Soc Rev. 2020 Dec 21;49(24):9095-9120
pubmed: 33118560
Chem Soc Rev. 2015 Sep 21;44(18):6616-43
pubmed: 26186682
Nat Chem. 2016 Dec;8(12):1120-1125
pubmed: 27874873
Nat Commun. 2016 Dec 07;7:13622
pubmed: 27924819
J Am Chem Soc. 2019 Nov 6;141(44):17558-17570
pubmed: 31604015
Angew Chem Int Ed Engl. 2019 Jan 2;58(1):86-116
pubmed: 30006951
Acc Chem Res. 2017 Feb 21;50(2):426-434
pubmed: 28068061
J Am Chem Soc. 2001 Jun 6;123(22):5337-47
pubmed: 11457397
J Chem Phys. 2019 Mar 28;150(12):124302
pubmed: 30927896
J Phys Chem A. 2019 Apr 4;123(13):2527-2536
pubmed: 30802051
Chem Rev. 2000 May 10;100(5):1789-1816
pubmed: 11777421