Thiophene-Fused Naphthodiphospholes: Modulation of the Structural and Electronic Properties of Polycyclic Aromatics by Precise Fusion of Heteroles.
charge transport
luminescence
organic materials
phospholes
thiophenes
Journal
ChemPlusChem
ISSN: 2192-6506
Titre abrégé: Chempluschem
Pays: Germany
ID NLM: 101580948
Informations de publication
Date de publication:
Jan 2021
Jan 2021
Historique:
received:
16
12
2020
revised:
17
12
2020
entrez:
8
1
2021
pubmed:
9
1
2021
medline:
9
1
2021
Statut:
ppublish
Résumé
For polycyclic aromatics with heterole-fused structures, the orientation of fused heterole rings as well as the geometry of their fused structures has a large impact on the physicochemical properties. In this study, a series of isomers of thiophene-fused naphthodiphospholes was designed and synthesized. Systematic investigation unveiled the explicit impact of heterole-fused structures on their structural and electronic properties. The isomers with 1,2/5,6-fused structure display phosphorescence due to enhanced spin-orbit coupling, whereas the isomers with 2,3/6,7-fused structure exhibit intense fluorescence. The trans isomers exhibited 1D slip π-stacked arrangement. In contrast, the cis isomers displayed 2D herringbone structure or columnar structure with a cavity. Therefore, the precisely controlled fusion of heterole rings is a universal approach to uncover their intrinsic properties for versatile applications as organic functional materials.
Identifiants
pubmed: 33415824
doi: 10.1002/cplu.202000800
doi:
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
130-136Subventions
Organisme : JSPS
ID : JP20H05841
Organisme : JSPS
ID : JP20H05840
Organisme : JSPS
ID : JP20H05836
Organisme : JSPS
ID : JP18H03898
Organisme : JSPS
ID : JP20H05832
Organisme : Shorai Foundation for Science and Technology
Organisme : Kyoto University Foundation
Informations de copyright
© 2020 Wiley-VCH GmbH.
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Crystallographic data for 1-trans: 0.5(C30H18O2P2S2), Mr=268.25, monoclinic, space group P21/a (No.14), a=9.937(5), b=12.080(6), c=10.521(5) Å, V=1260.2(11) Å3, ρcalcd=1.414 g cm−3, Z=4, 9965 reflections measured, 2836 unique (Rint=0.0507), R1=0.0396 [I>2σ(I)], wR2=0.0898 [all data], GOF=1.018; Crystallographic data for 2-trans: 0.5(C30H18O2P2S2) ⋅ C2H2Cl4, Mr=436.09, triclinic, space group P-1 (No.2), a=7.0282(15), b=11.267(2), c=12.639(3) Å, V=907.7(3) Å3, ρcalcd=1.596 g cm−3, Z=2, 7402 reflections measured, 3974 unique (Rint=0.0286), R1=0.0432 [I>2σ(I)], wR2=0.0976 [all data], GOF=1.030; Crystallographic data for 2-cis: C30H18O2P2S2, Mr=536.50, monoclinic, space group P21/n (No.14), a=12.839(5), b=8.355(3), c=23.324(10) Å, V=2411.7(17) Å3, ρcalcd=1.478 g cm−3, Z=4, 19072 reflections measured, 5588 unique (Rint=0.0371), R1=0.0390 [I>2σ(I)], wR2=0.1046 [all data], GOF=1.051; Crystallographic data for 3-cis: 0.5(C30H18O2P2S2) ⋅ 0.5(H2O), Mr=277.26, orthorhombic, space group Fddd (No.70), a=8.105(3), b=29.815(11), c=42.596(16) Å, V=10293(7) Å3, ρcalcd=1.431 g cm−3, Z=32, 19770 reflections measured, 2947 unique (Rint=0.0536), R1=0.0548 [I>2σ(I)], wR2=0.1508 [all data], GOF=1.029. Deposition Numbers CCDC 2036180 (for 1-trans), 2036178 (for 2-trans), 2036181 (for 2-cis), and 2036179 (for 3-cis) contain(s) the supplementary crystallographic data for this paper. These data are provided free of charge by the joint Cambridge Crystallographic Data Centre and Fachinformationszentrum Karlsruhe Access Structures service www.ccdc.cam.ac.uk/structures.
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