5-Methyl-1,3-phenyl-ene bis-[5-(di-methyl-amino)-naphthalene-1-sulfonate]: crystal structure and DFT calculations.

Tanwawan Duangthongyou,Songwut Suramitr,Boontana Wannalerse,Ramida Rattanakam,Thawatchai Tuntulani,Kittipong Chainok

doi:10.1107/s2056989019009058

Abstract

The title compound, C31H30N2S2O6, possesses crystallographically imposed twofold symmetry with the two C atoms of the central benzene ring and the C atom of its methyl substituent lying on the twofold rotation axis. The two dansyl groups are twisted away from the plane of methyl-phenyl bridging unit in opposite directions. The three-dimensional arrangement in the crystal is mainly stabilized by weak hydrogen bonds between the sulfonyl oxygen atoms and the hydrogen atoms from the N-methyl groups. Stacking of the dansyl group is not observed. From the DFT calculations, the HOMO-LUMO energy gap was found to be 2.99 eV and indicates n→π* and π→π* transitions within the mol-ecule.

Highlights

Chemical contextDansyl probes play important roles in many fields, including their use as industrial tracers and labelled biological tags (Tondi et al, 2005; Li et al, 2006; Liu et al, 2016)
The title compound, C31H30N2S2O6, possesses crystallographically imposed twofold symmetry with the two C atoms of the central benzene ring and the C atom of its methyl substituent lying on the twofold rotation axis
The three-dimensional arrangement in the crystal is mainly stabilized by weak hydrogen bonds between the sulfonyl oxygen atoms and the hydrogen atoms from the N-methyl groups

Summary

Chemical context

Dansyl probes play important roles in many fields, including their use as industrial tracers and labelled biological tags (Tondi et al, 2005; Li et al, 2006; Liu et al, 2016). Modified oligonucleotides that contain a dansyl fluorophore and (S)-2, 3-dihydroxy propyl carbamates linked to guanine residues result in an enhancement of the fluorescence. Such modified oligonucleotides can be used to prepare and detect the sequence of fluorogenic probes in DNA (Suzuki et al, 2013). Cu-labelled dansyl molecules have been designed and synthesized as fluorescence probes for membrane tags on apoptosis cells. These compounds can be used for PET imaging of the apoptosis in vivo (Han et al, 2016). Symmetry codes: (i) x þ 12; y þ 12; z; (ii) x; Ày þ 1; z À 12; (iii) x þ 12; y À 12; z

Structural commentary

Supramolecular features

Database survey

Synthesis and crystallization

Refinement