Features of styryl dye crystal packings and their influence on [2 + 2] photocycloaddition reaction with single crystal retention

DOI: 10.1039/C5CE00653H

Authors: Lyudmila G. Kuz'Mina (N. S. Kurnakov Institute of General and Inorganic Chemistry, Russian Academy of Sciences) , Artem I. Vedernikov (Photochemistry Center, Russian Academy of Sciences) , Judith Howard (University of Durham) , Michael V. Alfimov (Photochemistry Center, Russian Academy of Sciences) , Sergey P. Gromov (Photochemistry Center, Russian Academy of Sciences)
Co-authored by industrial partner: No

Type: Journal Paper
Journal: Crystengcomm , VOL 17 , PAGES 4584 - 4591

State: Published (Approved)
Published: May 2015
Diamond Proposal Number(s): 8682

Abstract: A new styryl dye of the 2-benzothiazole series which contains three methoxy groups and an iodide anion was synthesized. Three triclinic crystal forms of this dye were investigated by single crystal X-ray diffraction. All the modifications were shown to contain centrosymmetrically related stacks of cations with the syn-“head-to-tail” mutual arrangement. Stacks of cations are arranged as dimeric pairs with short interatomic distances between the ethylene group carbon atoms, d1 = 3.54–3.75 Å and significantly longer analogous distances between the adjacent pairs, d2 = 4.61–4.68 Å. The main difference of the packing consists in various orientations of N-ethyl substituents with respect to the centre of the dimer. The solid phase [2 + 2] photocycloaddition (PCA) reaction resulting in rctt isomer of the cyclobutane derivative, only proceeds in pairs where N-substituents are oriented outward from the centre of the dimeric pair. PCA is accomplished as a “single crystal-to-single crystal” transformation.

Subject Areas: Chemistry


Instruments: I19-Small Molecule Single Crystal Diffraction

Added On: 12/01/2016 11:53

Documents:
c5ce00653h.pdf

Discipline Tags:

Chemistry Organic Chemistry

Technical Tags:

Diffraction Single Crystal X-ray Diffraction (SXRD)