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

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

doi:10.1107/S2056989019009058

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

Acta Crystallogr E Crystallogr Commun. 2019 Jun 28;75(Pt 7):1079-1083. doi: 10.1107/S2056989019009058. eCollection 2019 Jul 1.

Authors

Tanwawan Duangthongyou¹, Ramida Rattanakam², Kittipong Chainok³, Songwut Suramitr⁴, Thawatchai Tuntulani⁵, Boontana Wannalerse¹

Affiliations

¹ Department of Chemistry and Center of Excellent for Innovation in Chemistry, Faculty of Science, Kasetsart University, Bangkok 10903, Thailand.
² Department of Chemistry, Faculty of Science, Kasetsart University, Bangkok 10903, Thailand.
³ Materials and Textile Technology, Faculty of Science, and Technology, Thammasart University, Pathum Thani 12120, Thailand.
⁴ Center of Nanotechnology, Department of Chemistry, Faculty of Science, Kasetsart University, Bangkok 10903, Thailand.
⁵ Supramolecular Chemistry Research Unit, Department of Chemistry, Faculty of Science, Chulalongkorn University, Bangkok 10330, Thailand.

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.

Keywords: 3,5-dihydroxytoluene; DFT calculations; crystal structure; dansyl unit; hydrogen bonds.