Open AccessApplication of Near‐IR Absorption Porphyrin Dyes Derived from Click Chemistry as Third‐Order Nonlinear Optical Materials
Author(s) -
Mi Yongsheng,
Liang Pengxia,
Yang Zhou,
Wang Dong,
Cao Hui,
He Wanli,
Yang Huai,
Yu Lian
Publication year - 2016
Publication title -
chemistryopen
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.644
H-Index - 29
ISSN - 2191-1363
DOI - 10.1002/open.201500124
Subject(s) - porphyrin , click chemistry , tetracyanoethylene , photochemistry , chemistry , cycloaddition , materials science , surface modification , combinatorial chemistry , organic chemistry , catalysis
Recently, third‐order nonlinear properties of porphyrins and porphyrin polymers and coordination compounds have been extensively studied in relation to their use in photomedicine and molecular photonics. A new functionalized porphyrin dye containing electron‐rich alkynes was synthesized and further modified by formal [2+2] click reactions with click reagents tetracyanoethylene (TCNE) and 7, 7, 8, 8‐tetracyanoquinodimethane (TCNQ). The photophysical properties of these porphyrin dyes, as well as the click reaction, were studied by UV/Vis spectroscopy. In particular, third‐order nonlinear optical properties of the dyes, which showed typical D ‐π‐A structures, were characterized by Z‐scan techniques. In addition, the self‐assembly properties were investigated through the phase‐exchange method, and highly organized morphologies were observed by scanning electron microscopy (SEM). The effects of the click post‐functionalization on the properties of the porphyrins were studied, and these functionalized porphyrin dyes represent an interesting set of candidates for optoelectronic device components.