Axially chiral, 3,5-dihydro-4H-dinaphtho[2,1-c:1′,2′-e]azepine (dinaphthazepine) and 1,1′-binaphthyl- 2,2′-disulfonimide (dinaphthosulfonimide) moieties were rigidly connected via N-p-phenylene linkers to photochemically (E)/(Z)-isomerisable 1,2-diethynylethene scaffolds. The chemical stability of the resulting systems was found to be critically related to the other substituents on the central π-conjugated scaffold. High helical twisting power (HTP), up to 315 μm−1, for the induction of a cholesteric liquidcrystalline phase through doping of a nematic phase was measured, resulting from the introduction of the chiral, mesogenic 1,1′-binaphthyl motifs. Single crystal X-ray analysis revealed that the phenylene spacer is in π-conjugation with the N-atom of the dinaphthazepine but not with the N-atom of the dinaphthosulfonimide moiety. This difference in orientation results in visible-transparency in the electronic absorption spectrum and higher (E)/(Z)-photoisomerisation quantum yields of the dinaphthosulfonimide-derived chiral dopants, as compared to the dinaphthazepine systems, which feature intramolecular charge-transfer absorption in the visible region.

1,2-DI(PHENYLETHYNYL)ETHENES WITH AXIALLY CHIRAL, 2,2’-BRIDGED 1,1’-BINAPHTYL SUBSTITUENTS: POTENT CHOLESTERIC LIQUID-CRYSTAL INDUCERS / Y-L. Wu; F. Ferroni; S. Pieraccini; W. B. Schweizer; B. B. Frank; G. P. Spada; F. Diederich. - In: ORGANIC & BIOMOLECULAR CHEMISTRY. - ISSN 1477-0520. - STAMPA. - 10:(2012), pp. 8016-8026. [10.1039/c2ob25983d]

1,2-DI(PHENYLETHYNYL)ETHENES WITH AXIALLY CHIRAL, 2,2’-BRIDGED 1,1’-BINAPHTYL SUBSTITUENTS: POTENT CHOLESTERIC LIQUID-CRYSTAL INDUCERS

PIERACCINI, SILVIA;SPADA, GIAN PIERO;
2012

Abstract

Axially chiral, 3,5-dihydro-4H-dinaphtho[2,1-c:1′,2′-e]azepine (dinaphthazepine) and 1,1′-binaphthyl- 2,2′-disulfonimide (dinaphthosulfonimide) moieties were rigidly connected via N-p-phenylene linkers to photochemically (E)/(Z)-isomerisable 1,2-diethynylethene scaffolds. The chemical stability of the resulting systems was found to be critically related to the other substituents on the central π-conjugated scaffold. High helical twisting power (HTP), up to 315 μm−1, for the induction of a cholesteric liquidcrystalline phase through doping of a nematic phase was measured, resulting from the introduction of the chiral, mesogenic 1,1′-binaphthyl motifs. Single crystal X-ray analysis revealed that the phenylene spacer is in π-conjugation with the N-atom of the dinaphthazepine but not with the N-atom of the dinaphthosulfonimide moiety. This difference in orientation results in visible-transparency in the electronic absorption spectrum and higher (E)/(Z)-photoisomerisation quantum yields of the dinaphthosulfonimide-derived chiral dopants, as compared to the dinaphthazepine systems, which feature intramolecular charge-transfer absorption in the visible region.
2012
1,2-DI(PHENYLETHYNYL)ETHENES WITH AXIALLY CHIRAL, 2,2’-BRIDGED 1,1’-BINAPHTYL SUBSTITUENTS: POTENT CHOLESTERIC LIQUID-CRYSTAL INDUCERS / Y-L. Wu; F. Ferroni; S. Pieraccini; W. B. Schweizer; B. B. Frank; G. P. Spada; F. Diederich. - In: ORGANIC & BIOMOLECULAR CHEMISTRY. - ISSN 1477-0520. - STAMPA. - 10:(2012), pp. 8016-8026. [10.1039/c2ob25983d]
Y-L. Wu; F. Ferroni; S. Pieraccini; W. B. Schweizer; B. B. Frank; G. P. Spada; F. Diederich
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11585/128047
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