2-Methoxynaphthalene at 173K

Bolte, Michael; Bauch, Christopher G.

doi:10.1107/s0108270198009330

Cited by 13 publications

(13 citation statements)

References 3 publications

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“…Despite this deviation, the sum of the internal angles in the iridabenzene ring is 713°, very close to 720° of benzene. In addition, the C−C bonds are in similar range with those found in 2‐methoxynaphthalene and our previously reported iridanaphthalene complexes . Overall, these facts suggest a remarkable π‐conjugation in our system.…”

Section: Figuresupporting

confidence: 88%

Spirobifluorene Metallaaromatics

Arias‐Coronado

Pereira-Cameselle

Ozcelik

et al. 2019

Chemistry A European J

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Spirobifluorene derivatives find use in many end-user applications. Therefore, furthere xpansiono f their scopei st he focus of many research studies. However,a lthough the optical properties of spirobifluorenes can be greatly tuned through incorporation of metal complexes,t od ate, spirobifluorene metallaaromatics remain unknown. Ta king advantage of the versatility of our methodologyf or the synthesis of metallaaromatic systems, this work reports the first metallaaromatic spirobifluorene compound. The presence of an Ir atom was found to redshift the absorption maximum by ca. 1.1 eV comparedt o bare spirobifluorene. Additionally,X -ray analysisa sw ell as anisotropy of the current-induced density calculations revealed this compound to be of aromatic nature.T he high stabilityi ns olution, solids tate, under air,a nd at high temperature, as well as distinct optical properties of this new class of compounds are expected to open new frontiers for chiroptical and optoelectronica pplications.

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Section: Figuresupporting

confidence: 88%

Spirobifluorene Metallaaromatics

Arias‐Coronado

Pereira-Cameselle

Ozcelik

et al. 2019

Chemistry A European J

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“…agreement with the corresponding distances in the simple analogues of (I), such as (II), (III), (IV), (V) and (VI) [1.376 (1), 1.377, 1.385, 1.394 (3) and 1.379 (4) Å , respectively], and the lengths of the C4-O2 and O2-C11 bonds compare well with those found in (VII) and in the methoxy derivatives of naphthalene such as 2-methoxynaphthalene [C ar -O = 1.3749 (11) Å and O-C methyl = 1.4250 (14) Å ; CSD refcode SAYRIT (Bolte & Bauch, 1998)], 1,4-dimethoxynaphthalene [C ar -O = 1.37 (1) and 1.39 (1) Å , and O-C methyl = 1.46 (1) and 1.44 (1) Å ; CSD refcode ALUJIA (Wiedenfeld et al, 1999)] and 1,8-dimethoxynaphthalene [C ar -O = 1.359 (2) and 1.362 (2) Å , and O-C methyl = 1.425 (2) and 1.419 (2) Å ; CSD refcode KEPKUL (Cosmo et al, 1990)] and with the values given by Allen & Kirby (1984). The ten-membered aromatic ring formed by atoms C1-C10 is planar, with the largest out-of-plane deviation of À0.015 (2) Å for atom C9.…”

Section: Figuresupporting

confidence: 62%

4-Methoxy-1-naphthol: chains formed by O—H...O hydrogen bonds and π–π stacking interactions

Marciniak

Różycka‐Sokołowska

2009

Acta Crystallogr C

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The structure of 4-methoxy-1-naphthol, C(11)H(10)O(2), (I), contains an intermolecular O-H...O hydrogen bond which links the molecules into a simple C(2) chain running parallel to the shortest crystallographic b axis. This chain is reinforced by intermolecular pi-pi stacking interactions. Comparisons are drawn between the crystal structure of (I) and those of several of its simple analogues, including 1-naphthol and some monosubstituted derivatives, and that of its isomer 7-methoxy-2-naphthol. This comparison shows a close similarity in the packing of the molecules of its simple analogues that form pi-stacks along the shortest crystallographic axes. A substantial spatial overlap is observed between adjacent molecules in such stacks. In this group of monosubstituted naphthols, the overlap depends mainly on the position of the substituents carried by the naphthalene moiety, and the extent of the overlap depends on the substituent type. By contrast with (I), in the crystal structure of the isomeric 7-methoxy-2-naphthol there are no O-H...O hydrogen bonds or pi-pi stacking interactions, and sheets are formed by O-H...pi and C-H...pi interactions.

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“…X‐ray crystallography13 proves that the almost planar cis configuration of 1 is the energetically favorable form in the ground state. Similarly, the crystal structure14 of 3 (Figure 1) shows that it crystallizes as a nearly planar molecule with each OG (G: C 7 H 15 O 3 ) group adopting a synperiplanar ( cis ) conformation (dihedral ϕ (C2‐C3‐O1‐C6)=6.7°).…”

Section: Methodsmentioning

confidence: 96%