Steric group enforced aromatic cyclic trimer conformer in tripodal molecules

Sathiyashivan, Shankar Deval; Shankar, Bhaskaran; Rajakannu, Palanisamy; Vishnoi, Pratap; Masram, Dhanraj T.; Sathiyendiran, Malaichamy

doi:10.1039/c5ra05151g

Cited by 6 publications

(3 citation statements)

References 36 publications

(23 reference statements)

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“…4 ). Due to the high presence of aromatic trimers with the cyclic and PD structures in proteins and DNA 6 , 22 , 23 and the essential role of secondary electrons for the radiation effects in gases and condensed matter 37 , 38 , the results obtained in this study could have important implications for a deeper and more complete understanding of radiation biology at the molecular level.…”

Section: Discussionmentioning

confidence: 89%

“…In biological systems, aromatic rings are often involved in more than one π - π interaction at a time, such as the stacking of nucleic acid bases in the double-helical structure of DNA 21 . In proteins as well, aromatic trimers are highly relevant for protein stability and molecular recognition processes due to the presence of aromatic trimer motifs in half of all proteins, and such motifs are built by adopting the same structures found for benzene trimers in a vacuum, which is thought of as the basic building unit of higher-order aromatic clusters 6 , 22 , 23 . It is therefore critical to elucidate the properties and dynamics of benzene trimers, which are of interest to a wide variety of research fields ranging from macromolecular sciences to astrochemistry 1 – 5 , 25 , 26 .…”

Section: Introductionmentioning

confidence: 99%

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Triple ionization and fragmentation of benzene trimers following ultrafast intermolecular Coulombic decay

Zhou

Luo

et al. 2022

Nat Commun

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Intermolecular interactions involving aromatic rings are ubiquitous in biochemistry and they govern the properties of many organic materials. Nevertheless, our understanding of the structures and dynamics of aromatic clusters remains incomplete, in particular for systems beyond the dimers, despite their high presence in many macromolecular systems such as DNA and proteins. Here, we study the fragmentation dynamics of benzene trimer that represents a prototype of higher-order aromatic clusters. The trimers are initially ionized by electron-collision with the creation of a deep-lying carbon 2s−1 state or one outer-valence and one inner-valence vacancies at two separate molecules. The system can thus relax via ultrafast intermolecular decay mechanisms, leading to the formation of C$${}_{6}{{{{{{{{{\rm{H}}}}}}}}}_{6}}^{+}\cdot$$ 6 H 6 + ⋅ C$${}_{6}{{{{{{{{{\rm{H}}}}}}}}}_{6}}^{+}\cdot$$ 6 H 6 + ⋅ C$${}_{6}{{{{{{{{{\rm{H}}}}}}}}}_{6}}^{+}$$ 6 H 6 + trications and followed by a concerted three-body Coulomb explosion. Triple-coincidence ion momentum spectroscopy, accompanied by ab-initio calculations and further supported by strong-field laser experiments, allows us to elucidate the details on the fragmentation dynamics of benzene trimers.

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Section: Discussionmentioning

confidence: 89%

Section: Introductionmentioning

confidence: 99%

Triple ionization and fragmentation of benzene trimers following ultrafast intermolecular Coulombic decay

Zhou

Luo

et al. 2022

Nat Commun

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“…However, the methylene protons (−C H 2 −) appeared as a singlet chemical resonance at δ 4.79. In general, the methylene protons in R–C H 2 –R 1 (R = benzene and R 1 = imidazolyl/benzimidazolyl) appear either as a singlet with/without broadening or a doublet with a geminal coupling constant in the δ 5.50–6.00 region. ,− The unusual upfield shift of the −C H 2 – proton signal of L 3 compared to those of the known di/tri/hexatopic imidazolyl/benzimidazolyl ligands ,− and L 2 indicates that the −C H 2 – protons experienced ring-current effects; i.e., they were located in the shielding zone of the arene units, from the adjacent phenylene units. The results indirectly support the formation of L 3 (Figures S3 and S4 in the SI).…”

Section: Resultsmentioning

confidence: 99%

Spheroid Metallacycles and Metallocavitands with Calixarene- and/or Cleft-Shaped Receptors on the Surface

et al. 2016

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Flexible hexatopic ligands, 1,2,3,4,5,6-hexakis(1H-naphtho[2,3-d]imidazol-1-ylmethyl)benzene (L(2)) and 1,2,3,4,5,6-hexakis(4,5-diphenylimidazol-1-ylmethyl)benzene (L(3)), containing six neutral naphthanoimidazolyl and 4,5-diphenylimidazolyl N donors were synthesized and used to assemble M6L6L'-type [M = Re(CO)3, L = anionic angular rigid NN donors, and L' = flexible hexatopic N donors] spheroid metallacycles. These molecules with a diameter of ∼17 Å were obtained from Re2(CO)10, H-L (imidazole, benzimidazole, and naphthanoimidazole), and L' [1,2,3,4,5,6-hexakis(benzimidazol-1-ylmethyl)benzene (L(1)), L(2), and L(3)] in a one-step process. Ligands L(2) and L(3) were characterized by elemental analysis, electrospray ionization time-of-flight mass spectrometry (ESI-TOF-MS), and (1)H NMR spectroscopy. Metallacycles 1-5 were characterized by elemental analysis, ESI-TOF-MS, Fourier transform infrared spectroscopy, and single-crystal X-ray diffraction analysis. Molecules 1, 2, and 4 can be considered as metallocavitands and contain multiple solvent-accessible receptors, i.e., two metallocalix[3]arene units and six/four calix[4]arene-/cleft-shaped receptors, on the surface. Guests such as acetone molecules could be accommodated in the calix[4]arene/cleft-shaped receptor of the metallocavitands.

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fac-Re(CO)3-based organometallic supramolecular coordination complexes using thiophene motif decorated flexible ditopic benzimidazolyl donor

Rajakannu

Shankar

Sathiyendiran

2018

Journal of Organometallic Chemistry

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Steric group enforced aromatic cyclic trimer conformer in tripodal molecules

Abstract: A family of tripodal molecules (1–6) with/without steric ethyl groups at the central benzene scaffold and with furan/thiophene/pyridyl groups at the 2-position of the benzimidazolyl unit was synthesised.

Cited by 6 publications

References 36 publications

Triple ionization and fragmentation of benzene trimers following ultrafast intermolecular Coulombic decay

Triple ionization and fragmentation of benzene trimers following ultrafast intermolecular Coulombic decay

Spheroid Metallacycles and Metallocavitands with Calixarene- and/or Cleft-Shaped Receptors on the Surface

fac-Re(CO)3-based organometallic supramolecular coordination complexes using thiophene motif decorated flexible ditopic benzimidazolyl donor

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