X-ray crystal structures of p-halogenated 6,6-diphenylfulvenes

Schwarzer, Anke; Seichter, Wilhelm; Weber, Edwin

doi:10.1007/s11224-010-9685-8

Cited by 9 publications

(9 citation statements)

References 33 publications

(54 reference statements)

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“…Other relations between the crystal structures of chlorine, bromine and iodine derivatives were, for example, observed for halogenated benzils, diphenylhexatrienes and 6,6‐diphenylfulvenes . While the bromine and iodine derivatives of benzil are reported to be isostructural, the corresponding chlorine derivative has been found to crystallize different.…”

Section: Resultsmentioning

confidence: 90%

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Fluorene Derivatives Bearing Halogenomethyl Groups: Synthesis, Molecular Structures, and Halogen/Hydrogen Bonding Patterns in the Crystalline State

2019

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9,9‐Diethylfluorenes bearing chloromethyl, bromomethyl, and iodomethyl groups in the 2, 4, and 7 positions of the aromatic skeleton were prepared and their solid‐state structures determined by single‐crystal X‐ray diffraction analysis. The prepared fluorenes represent not only valuable starting materials for a wide range of fluorene‐based compounds but are also interesting objects for the analysis of the supramolecular motifs in the crystalline state. The X‐ray diffraction experiments revealed that the asymmetric unit of each structure contains one molecule, featuring similar conformations, but differ in their modes of non‐covalent intermolecular bonding. The crystal structures of the chloromethyl and bromomethyl substituted compounds 1 and 2 are primarily stabilized by Hal···Hal and C–H···Hal contacts, whereas the packing of the iodine substituted analogous compound 3 is influenced by triangular I3 synthons, C–H···π interactions and to a less degree by C–H···I contacts. The manuscript provides information about new synthetic routes, new molecules as well as about halogen/hydrogen bonding patterns and other noncovalent interactions in the crystalline state. Concerning the syntheses, the efficient one‐step synthesis of 9,9‐diethylfluorene‐2,4,7‐tricarbaldehyde (8) is also worthy of particular mention.

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Section: Resultsmentioning

confidence: 90%

“…While the bromine and iodine derivatives of benzil are reported to be isostructural, the corresponding chlorine derivative has been found to crystallize different. In the case of the halogenated diphenylhexatrienes and 6,6‐diphenylfulvenes the chlorine, bromine and iodine derivatives are reported to be isostructural.…”

Section: Resultsmentioning

confidence: 99%

Fluorene Derivatives Bearing Halogenomethyl Groups: Synthesis, Molecular Structures, and Halogen/Hydrogen Bonding Patterns in the Crystalline State

2019

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“…In the crystallographic study by Schwarzer et al [34], p-halogenated (with fluorine, chlorine, bromine, and iodine) 6,6-diphenylfulvenes were synthesized and their X-ray crystal structures determined and compared to the known structure of the nonhalogenated parent compound. The twisting of the planar subunits is not particularly affected by the different halogen substituents.…”

Section: Issuementioning

confidence: 99%

Interplay of thermochemistry and Structural Chemistry, the Journal (volume 22, 2011, issues 1–3) and the discipline

Ponikvar‐Svet

Liebman

2011

Struct Chem

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“…Calixarenes containing modified meso bridges [46][47][48] are synthesized via substitution of methylene bridges [49][50][51][52] or via their oxidation to keto groups; 53,54 they have not been as intensively studied as calixarenes functionalized at wide 55,56 or narrow 57.58 rims. Therefore it seems of interest to describe several selected examples of this class of compounds, showing their possible applications.…”

Section: Introductionmentioning

confidence: 99%