Spectral and photochemical properties of bis(styrylquinoline) dyad with o-xylylene bridge

Abstract

Properties of 1,2 bis (4 [(E) 2 quinoline 2 vinyl)phenoxymethyl)benzene, a bis(styrylquino line) dyad SoS, in which two styrylquinoline fragments (SQ) are linked by o xylylene bridge, have been inves tigated. Photoisomerization of the SQ fragment in the bichromophoric dyad occurs as efficiently as in the monochromophoric model compound 2 (4 methoxystyryl)quinoline MeSQ. Along with photoisomeriza tion, [2 + 2] photocycloaddition occurs affording tetrasubstituted cyclobutane. According to the quantum chemical DFT calculations, this reaction is assisted by preorganizing action of o xylylene group orienting the two SQ fragments in the dyad in the head to head position.

Irreversible One‐Way [2+2] Photocycloaddition in Bis‐Styrylbenzo[f]quinoline Dyad: Photoactive and Photoinert Excimers in the Same System

“…As can be seen in Figure , PCA proceeded quantitatively until complete consumption of the starting dyad. In general, PCA is a reversible reaction, and complete transformation of one isomer to another is sometimes possible only if one of isomers does not absorb an incident light. However, it is not relevant to this case: 4 has low but noticeable absorbance at 370 nm (MAC=4300 M −1 cm −1 ).…”

Functionalized benzazines as luminescent materials and components for optoelectronics

“…When the polyethylene linker incorporate an o-xylylene bridge (compound 20), along with photoisomerization, [2+2]-photocycloaddition occurs affording tetrasubstituted cyclobutane (Scheme 5). 40 When one of the two 2-stryrylquinoline is replaced by a styrylquinolinium fragment (dyad 19), [41][42][43] photoisomerization of the styrylquinoline fragment occurs only on one-way: it goes in cistrans direction whereas transcis isomerization is quenched because of competing FRET to the styrylquinolinium fragment. Nevertheless, transcis photoisomerization can be observed upon protonation of the styrylquinoline fragment.…”

Photonics of styrylquinoline dyads

“…The bis-styrylquinoline dyad SoS (1,2-bis-(E)-(4-[(2-quinolin-2-yl-vinyl)-phenoxymethyl])benzene), where two SQ fragments are linked by ortho-xylylene group, was synthesized by alkylation of (E)-2-(4-hydroxystyryl)quinoline with 1,2-bis(bromomethyl)benzene, Scheme 6 [38,39] Scheme 6: Synthesis of bis-styrylquinoline dyad SoS.…”