Molecular curvature tradeoffs: Bending a planar trimercury unit over bowl-shaped polyaromatic hydrocarbons

Filatov, Alexander S.; Greene, Allison K.; Jackson, Edward A.; Scott, Lawrence T.; Petrukhina, Marina A.

doi:10.1016/j.jorganchem.2011.01.038

Cited by 39 publications

(31 citation statements)

References 33 publications

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“…As a result, obtained energy gap is higher than the energy gap (2.36 eV) calculated from the electrochemical measurements of the oxidation potential of DTT (1) i For triphenylene, see [28], and the larger aromatic hydrocarbons, see [43]. Co-crystals with macrocycle I were reported as white solid.…”

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confidence: 75%

“…Here, we report the X-ray single crystal analysis of the DTT and its mixed-stack complexes with trimeric perfluoroo-phenylene mercury (I) (Chart 1), an acceptor known to form mixed-stack co-crystals with a variety of donors [28][29][30]. Unexpectedly, two different mixed-stack complexes 2 and 3 were obtained from carbon disulfide-dichloromethane (DCM) and carbon disulfide-dichloroethane (DCE) solutions, respectively; in both cases the chlorinated solvent co-crystallized with the DTTmacrocycle I co-crystals.…”

Section: Introductionmentioning

confidence: 99%

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Mixed-stack architecture and solvatomorphism of trimeric perfluoro-ortho-phenylene mercury complexes with dithieno[3,2-b:2′,3′-d]thiophene

Castañeda

Khrustalev

Fonari

et al. 2015

Journal of Molecular Structure

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confidence: 75%

Section: Introductionmentioning

confidence: 99%

Mixed-stack architecture and solvatomorphism of trimeric perfluoro-ortho-phenylene mercury complexes with dithieno[3,2-b:2′,3′-d]thiophene

Castañeda

Khrustalev

Fonari

et al. 2015

Journal of Molecular Structure

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“…In this regard, we decided to focus on dibenzo[ a , g ]corannulene (C 28 H 14 , Scheme left) that consists of a central corannulene core fused with two peripheral benzene rings on the rim. The bowl‐shaped geometry of C 28 H 14 was revealed back in 2005 but only two examples of metal complexation have been reported since then . Stepwise reduction of C 28 H 14 was studied in solution by Rabinovitz and Scott with co‐workers using spectroscopic techniques .…”

Section: Methodsmentioning

confidence: 99%

Site‐Directed Dimerization of Bowl‐Shaped Radical Anions to Form a σ‐Bonded Dibenzocorannulene Dimer

et al. 2018

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Designed site-directed dimerization of the monoanion radicals of a p-bowl in the solid state is reported. Dibenzo[a,g]corannulene (C 28 H 14 )w as selected based on the asymmetry of the charge/spin localization in the C 28 H 14 C À anion. Controlled one-electron reduction of C 28 H 14 with Cs metal in diglyme resulted in crystallization of an ew dimer, [{Cs + (diglyme)} 2 (C 28 H 14 ÀC 28 H 14 ) 2À ]( 1), as revealed by single crystal X-rayd iffraction study performed in ab road range of temperatures.T he C À Cb ond length between two C 28 H 14 C À bowls (1.560 (8) )measured at À143 8 8Cdoes not significantly change upon heating of the crystal to + 67 8 8C. The single sbond character of the CÀClinker is confirmed by calculations. The trans-disposition of two bowlsi n1 is observed with the torsion angles around the central CÀCb ond of 172.3(5)8 8 and 173.5(5)8 8.Asystematic theoretical evaluation of dimerization pathwayso fC 28 H 14 C À radicals confirmed that the trans-isomer found in 1 is energetically favored.Supportinginformation and the ORCID identification number(s) for the author(s) of this article can be found under: https://doi.org/10.1002/anie.201801537. Scheme 1. Dibenzo[a,g]corannulene (left) and (C 28 H 14 ÀC 28 H 14 ) 2À dimer (right).

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“…In the last decades, there has been considerable interest in the binding and catalytic properties of macrocyclic multidentate Lewis acids representing antipodes of conventional crown compounds and called anticrowns (see reviews and papers cited in refs). These remarkable reagents exhibit a high affinity toward various anions and neutral Lewis bases forming complexes with them wherein the Lewis basic species is cooperatively coordinated by all Lewis acidic centers of the anticrown.…”

Section: Introductionmentioning

confidence: 99%

Coordination Chemistry of Anticrowns. Synthesis and Structures of Complexes of the Perfluorinated Three‐Mercury Anticrown (o‐C₆F₄Hg)₃ with Monohalogenobenzenes

et al. 2019

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Molecular curvature tradeoffs: Bending a planar trimercury unit over bowl-shaped polyaromatic hydrocarbons

Cited by 39 publications

References 33 publications

Mixed-stack architecture and solvatomorphism of trimeric perfluoro-ortho-phenylene mercury complexes with dithieno[3,2-b:2′,3′-d]thiophene

Mixed-stack architecture and solvatomorphism of trimeric perfluoro-ortho-phenylene mercury complexes with dithieno[3,2-b:2′,3′-d]thiophene

Site‐Directed Dimerization of Bowl‐Shaped Radical Anions to Form a σ‐Bonded Dibenzocorannulene Dimer

Coordination Chemistry of Anticrowns. Synthesis and Structures of Complexes of the Perfluorinated Three‐Mercury Anticrown (o‐C₆F₄Hg)₃ with Monohalogenobenzenes

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Molecular curvature tradeoffs: Bending a planar trimercury unit over bowl-shaped polyaromatic hydrocarbons

Cited by 39 publications

References 33 publications

Mixed-stack architecture and solvatomorphism of trimeric perfluoro-ortho-phenylene mercury complexes with dithieno[3,2-b:2′,3′-d]thiophene

Mixed-stack architecture and solvatomorphism of trimeric perfluoro-ortho-phenylene mercury complexes with dithieno[3,2-b:2′,3′-d]thiophene

Site‐Directed Dimerization of Bowl‐Shaped Radical Anions to Form a σ‐Bonded Dibenzocorannulene Dimer

Coordination Chemistry of Anticrowns. Synthesis and Structures of Complexes of the Perfluorinated Three‐Mercury Anticrown (o‐C6F4Hg)3 with Monohalogenobenzenes

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Coordination Chemistry of Anticrowns. Synthesis and Structures of Complexes of the Perfluorinated Three‐Mercury Anticrown (o‐C₆F₄Hg)₃ with Monohalogenobenzenes