Antiaromatic Supramolecules: F⋅⋅⋅S, F⋅⋅⋅Se, and F⋅⋅⋅π Intermolecular Interactions in 32 π Expanded Isophlorins

Gopalakrishna, Tullimilli Y.; Reddy, J. Sreedhar; Anand, Venkataramanarao G.

doi:10.1002/ange.201207987

Cited by 8 publications

(2 citation statements)

References 50 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…In addition to C-H···F interactions, F···X (X=S, π) interactions are the other relatively weak interactions that have recently been recognized in organic fluorinated molecules [20][21][22][23][24]. It is now well-established that drug molecules containing one or more fluorine atoms show superior biological properties as compared to their non-fluorinated analogues perhaps due to better interactions with the receptor sites in our body [25].…”

Section: Introductionmentioning

confidence: 96%

Synthesis and fluorine-mediated interactions in methanol-encapsulated solid state self-assembly of an isatin-thiazoline hybrid

Pervez

Ahmad

Hadda

et al. 2015

Journal of Molecular Structure

View full text Add to dashboard Cite

International audienceAn exciting isatin-thiazoline hybrid molecule 2 having -C=N-N=C- linkage has been synthesized in 88% yield by the reaction of 5-fluoroisatin with N-(4-fluorophenyl)hydrazinecarbothioamide followed by condensation of the resultant isatin-thiosemicarbazone intermediate with p-chlorophenacyl bromide. The solid state self-assembly of this hybrid molecule was studied by X-ray crystallographic technique. A layered assembly composed of 1D-chains with methanol molecules encapsulated between every two chains is obtained, making a bi-chain sandwich like structure. The supramolecular forces involved in the stabilization of this structure are importantly fluorine-mediated interactions (C-H···F, F···S and F···π) along with others i.e. N-H···O, O-H···O, C-H···O, Cl···π, C-H···π and π···π interactions. To the best of our knowledge, this is the first example of solid state fluorine-mediated C-H···F, F···S and F···π interactions found in a family of isatin-based compound

show abstract

Section: Introductionmentioning

confidence: 96%

Synthesis and fluorine-mediated interactions in methanol-encapsulated solid state self-assembly of an isatin-thiazoline hybrid

Pervez

Ahmad

Hadda

et al. 2015

Journal of Molecular Structure

View full text Add to dashboard Cite

show abstract

“…We synthesized derivatives of the antiaromatic 32π‐expanded isophlorin11 1 to study their structural conformation with a varying ratio of furan and thiophene rings (Figure 1). The macrocycles 2 – 5 were synthesized by an acid‐catalyzed condensation of E ‐ethylene bridged bis(thiophene)/furan with the corresponding diols, followed by oxidation 11. Apart from the expected product, very low yields of larger macrocycles were also detected in the MALDI‐TOF mass spectrum of the reaction mixture.…”

mentioning

confidence: 99%

Reversible Redox Reaction Between Antiaromatic and Aromatic States of 32π‐Expanded Isophlorins

Gopalakrishna

Anand

2014

Angewandte Chemie

Self Cite

View full text Add to dashboard Cite

32p-antiaromatic expanded isophlorins with a varying number of thiophene and furan rings adopt either planar, ring-inverted, or twisted conformations depending on the number of furan rings in the macrocycle. However, they exhibit identical reactivity with respect to their oxidation to aromatic 30p-dicationic species under acidic conditions. These 32p-antiaromatic macrocycles can also be oxidized with [Et 3 O + SbCl 6 À ]and NOBF 4 to generate dications, thus confirming ring oxidation of macrocycles. Furthermore, they can be reduced back to their parent 32p-antiaromatic state by triethylamine, Zn, or FeCl 2 . Single-crystal X-ray diffraction analysis confirmed a figure-eight conformation for a hexafuran system, which opens to a planar structure upon oxidation.

show abstract

Cyclobis(7,8‐(para‐quinodimethane)‐4,4′‐triphenylamine) and Its Cationic Species Showing Annulene‐Like Global (Anti)Aromaticity

2019

Self Cite

View full text Add to dashboard Cite

p-Conjugated macrocycles containing all-benzenoid rings usually show local aromaticity,but reported herein is the macrocycle CBQT,c ontaining alternating para-quinodimethane and triphenylamine units displaying annulene-like antiaromaticity at low temperatures as aresult of structural rigidity and participation of the bridging nitrogen atoms in pconjugation. It was easily synthesized by intermolecular Friedel-Crafts alkylation followed by oxidative dehydrogenation. X-rayc rystallographic structures of CBQT,a sw ell as those of its dication, trication, and tetracation were obtained. The dication and tetracation exhibited global aromaticity and antiaromaticity,r espectively,a sconfirmed by NMR measurements and theoretical calculations.B oth the dication and tetracation possess open-shell singlet ground states,w ith as mall singlet-triplet gap.

show abstract

Antiaromatic Supramolecules: F⋅⋅⋅S, F⋅⋅⋅Se, and F⋅⋅⋅π Intermolecular Interactions in 32 π Expanded Isophlorins

Cited by 8 publications

References 50 publications

Synthesis and fluorine-mediated interactions in methanol-encapsulated solid state self-assembly of an isatin-thiazoline hybrid

Synthesis and fluorine-mediated interactions in methanol-encapsulated solid state self-assembly of an isatin-thiazoline hybrid

Reversible Redox Reaction Between Antiaromatic and Aromatic States of 32π‐Expanded Isophlorins

Cyclobis(7,8‐(para‐quinodimethane)‐4,4′‐triphenylamine) and Its Cationic Species Showing Annulene‐Like Global (Anti)Aromaticity

Contact Info

Product

Resources

About