Premium
Synthesis and electronic spectra of substituted oligo(phenylenevinylene)s
Author(s) -
Detert Heiner,
Sugiono Erli
Publication year - 2000
Publication title -
journal of physical organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.325
H-Index - 66
eISSN - 1099-1395
pISSN - 0894-3230
DOI - 10.1002/1099-1395(200010)13:10<587::aid-poc275>3.0.co;2-i
Subject(s) - chemistry , chromophore , bathochromic shift , solvatochromism , photochemistry , absorption (acoustics) , absorption spectroscopy , solubility , spectral line , molecule , fluorescence , organic chemistry , materials science , physics , astronomy , quantum mechanics , composite material
A series of substituted oligo( p ‐phenylenevinylene)s (OPVs) with five benzene rings was prepared via PO‐activated olefinations and Knoevenagel condensations. The central ring is substituted with two octyloxy groups to ensure good solubility of the OPVs and the lateral styrene units carry further substituents, with either electron‐accepting or donating character and also combinations thereof. The spectral features of these OPVs are dominated by the basic chromophore; further auxochrome groups on the lateral rings ( meta and para positions) shift the absorption and emission spectra only slightly to longer wavelengths. Significant bathochromic shifts (absorption ca 20 nm, emission ca 40 nm) are observed for OPVs with cyano groups on the terminal vinylene segments. The absorption spectra are independent from the concentration and solvatochromism is very small. The OPVs are photochemically stable to near‐UV irradiation (366 nm) in neutral solution, whereas mid‐UV irradiation (254 nm) causes decomposition of the chromophore. The presence of traces of acids or amines leads to different photochemical pathways. Copyright © 2000 John Wiley & Sons, Ltd.