TY - JOUR
T1 - The influence of a 1,1-diarylvinyl moiety on the photochromism of naphthopyrans
AU - Gabbutt, Christopher D.
AU - Heron, B. Mark
AU - Kilner, Colin
AU - Kolla, Suresh B.
PY - 2010/11/7
Y1 - 2010/11/7
N2 - 1,1,3-Triarylpent-4-en-1-yn-3-ols, efficiently obtained in two steps from 1,1,3-triarylprop-2-yn-1-ols by a Meyer-Schuster rearrangement and subsequent addition of lithium trimethylsilylacetylide, react with either a 1- or 2- naphthol to afford photochromic 1,1-diarylvinyl substituted naphtho[1,2-b]- or naphtho[2,1-b]-pyrans respectively. Irradiation of solutions of these naphthopyrans results in reversible electrocyclic ring-opening to afford photomerocyanines which possess an extended conjugated system and show a bathochromically-shifted λmax relative to the non-vinyl substituted analogues.
AB - 1,1,3-Triarylpent-4-en-1-yn-3-ols, efficiently obtained in two steps from 1,1,3-triarylprop-2-yn-1-ols by a Meyer-Schuster rearrangement and subsequent addition of lithium trimethylsilylacetylide, react with either a 1- or 2- naphthol to afford photochromic 1,1-diarylvinyl substituted naphtho[1,2-b]- or naphtho[2,1-b]-pyrans respectively. Irradiation of solutions of these naphthopyrans results in reversible electrocyclic ring-opening to afford photomerocyanines which possess an extended conjugated system and show a bathochromically-shifted λmax relative to the non-vinyl substituted analogues.
UR - http://www.scopus.com/inward/record.url?scp=77957924030&partnerID=8YFLogxK
U2 - 10.1039/c0ob00141d
DO - 10.1039/c0ob00141d
M3 - Article
AN - SCOPUS:77957924030
VL - 8
SP - 4874
EP - 4883
JO - Organic and Biomolecular Chemistry
JF - Organic and Biomolecular Chemistry
SN - 1477-0520
IS - 21
ER -