Bent π-conjugated system composed of two dibenzocyclooctatetraene units: Multifunctional properties of dynamic molecular tweezers in solution and the solid state

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[1] [1,Nishiuchi, Tomohiko

[2] Iyoda, Masahiko

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Iyoda, Masahiko | 1600年 / Chemical Society of Japan卷 / 87期

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A series of bent π-conjugated compounds; 2a; 2b; 3a; and; 3b; composed of two tub-shaped dibenzocyclooctatetraene (DBCOT) units with two cyano substituents on each cyclooctatetraene (COT) ring were designed and synthesized by using improved synthetic procedures. The anti- and syn-conformers of 2a; 2b and 3a; which coexist in equilibrium in solution; were independently observed by using 1HNMR spectroscopy at room temperature; and the signals of the anti-and syn-forms coalesced at 130°C to give signa ls assigned to a D2hsymmetric molecule. The ratio of the anti- and synisomers of these dynamic molecular tweezers (DMTs) were dependent on the position of the cyano substituents on the COT rings due to the difference in either torsional strain or dipole moments between the anti- and syn-isomers (2a; 2b:; syn; anti; 3b: syn 1HNMR and UV-vis spectroscopic titration experiments and evaluated on the basis of the calculated affinity for a guest molecule. We found that 2a; 3b exhibited unique aggregation-induced emission in solution and crystalline-state emission induced by incorporated solvents in the crystal lattices of the DMTs. The emission wavelength and quantum yield of the aggregation-induced and crystalline-state emissions depended on their restricted flexibility and syn-anti ratio. Theoretical calculations confirmed that the dihedral angle between the central and terminal benzene rings had the largest effect on the emission wave length in the crystalline state. © 2014 The Chemical Society of Japan;

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共 5 条

[1] Bent π-Conjugated System Composed of Two Dibenzocyclooctatetraene Units: Multifunctional Properties of Dynamic Molecular Tweezers in Solution and the Solid State
Nishiuchi, Tomohiko
Iyoda, Masahiko
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 2014, 87 (09) : 960 - 973
[2] Dynamic Molecular Tweezers Composed of Dibenzocyclooctatetraene Units: Synthesis, Properties, and Thermochromism in Host-Guest Complexes
Nishiuchi, Tomohiko
Kuwatani, Yoshiyuki
Nishinaga, Tohru
Iyoda, Vlasahiko
CHEMISTRY-A EUROPEAN JOURNAL, 2009, 15 (28) : 6838 - 6847
[3] Solvent-Induced Crystalline-State Emission and Multichromism of a Bent π-Surface System Composed of Dibenzocyclooctatetraene Units
Nishiuchi, Tomohiko
Tanaka, Keita
Kuwatani, Yoshiyuki
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Iyoda, Masahiko
CHEMISTRY-A EUROPEAN JOURNAL, 2013, 19 (13) : 4110 - 4116
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JOURNAL OF MATERIALS CHEMISTRY C, 2024, 12 (25) : 9112 - 9129

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