Synthesis and crystal structures of 5,5'-(propane-2,2-di-yl)bis-(2-hy-droxy-benzaldehyde) and 5,5'-(propane-2,2-di-yl)bis-(2-hy-droxy-isophthalaldehyde)

Rosario C Sausa; Dominika N Lastovickova; John J La Scala

doi:10.1107/S2056989018016316

Synthesis and crystal structures of 5,5'-(propane-2,2-di-yl)bis-(2-hy-droxy-benzaldehyde) and 5,5'-(propane-2,2-di-yl)bis-(2-hy-droxy-isophthalaldehyde)

Acta Crystallogr E Crystallogr Commun. 2018 Nov 22;74(Pt 12):1872-1877. doi: 10.1107/S2056989018016316. eCollection 2018 Dec 1.

Authors

Rosario C Sausa¹, Dominika N Lastovickova², John J La Scala²

Affiliations

¹ US Army Research Laboratory, RDRL-WML-B, Aberdeen Proving Ground, MD 21005, USA.
² US Army Research Laboratory, RDRL-WML-G, Aberdeen Proving Ground, MD 21005, USA.

Abstract

The title compounds 5,5'-(propane-2,2-di-yl)bis-(2-hy-droxy-benzaldehyde), C₁₇H₁₆O₄, (1), and 5,5'-(propane-2,2-di-yl)bis-(2-hy-droxy-isophthalaldehyde), C₁₉H₁₆O₆, (2), crystallize with one mol-ecule in the asymmetric unit. In mol-ecule (1), a >C(CH₃)₂ group bridges two nearly planar salicyl-aldehyde groups [r.m.s deviations = 0.010 (1) and 0.025 (2) Å], each comprising a planar phenyl ring bonded with a hydroxyl and an aldehyde group. Similarly, compound (2) has the same bridging group, but it connects two nearly planar appendants [r.m.s deviations = 0.034 (1) and 0.035 (1) Å], each comprising a phenyl ring bonded with a hydroxyl and two aldehyde groups. Mol-ecule (1) exhibits a bridge angle of 109.5 (2)° with the salicyl-aldehyde planes subtending a dihedral angle of 88.4 (1)°. In contrast, mol-ecule (2) presents a bridge angle of 108.9 (2)° with its appendants subtending a dihedral angle of 79.6 (3)°. Both mol-ecules exhibit two intra-molecular O-H⋯O hydrogen bonds involving the phenolic H atoms and carboxyl O-atom acceptors. In the crystal of (2), O-H⋯O hydrogen bonds between one of the hydroxyl H atoms and a carboxyl O atom from a symmetry-related mol-ecule form a chain along [10]. In addition, (2) exhibits a strong visible luminescence when excited with ultraviolet radiation.

Keywords: 5,5′-(propane-2,2-diyl)bis(2-hydroxybenzaldehyde); 5,5′-(propane-2,2-diyl)bis(2-hydroxyisophthalaldehyde); NMR; crystal structure; photoluminescence; synthesis.