Synthesis and fluorescence behavior of 2,5-diphenyl-1,3,4-oxadiazole-containing bismaleimides and bissuccinimides

doi:10.1007/s11705-013-1359-9

Front Chem Sci Eng

2013, Vol. 7

Issue (4) : 381-387 https://doi.org/10.1007/s11705-013-1359-9

RESEARCH ARTICLE

Synthesis and fluorescence behavior of 2,5-diphenyl-1,3,4-oxadiazole-containing bismaleimides and bissuccinimides

Xin ZHANG¹(

), Zichen LI²

1. University of Wuerzburg, Institute of Organic Chemistry, Am Hubland, 97074 Wuerzburg, Germany; 2. Key Laboratory of Polymer Chemistry & Physics of Ministry of Education, College of Chemistry & Molecular Engineering, Peking University, Beijing 100871, China

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Abstract

Bismaleimides bearing 2,5-diphenyl-1,3,4-oxadiazole chromophores at para, meta, ortho position and corresponding saturated bissuccinimides were synthesized. Several synthetic strategies for these bismaleimides were discussed in detail. Almost no or very weak fluorescence was observed for these bismaleimides, however, the bissuccinimides show a strong fluorescence. The effect of molecular geometry on optical behavior and fluorescence quenching mechanism were investigated by UV-vis absorption and fluorescence emission spectroscopy. The electron coupling of ground state of p-bismaleimide is stronger than those of m- and o-bismaleimides. p-Bissuccinimide displays increasing fluorescence quantum yields with red shifts of 22–24 nm, compared to m-bissuccinimide. Polymerizable C=C bonds play a key role in the intramolecular fluorescence quenching.

Keywords fluorescence bismaleimide oxadiazole succinimide

Corresponding Author(s): ZHANG Xin,Email:xin.zhang@uni-wuerzburg.de

Issue Date: 05 December 2013

Cite this article:

Xin ZHANG,Zichen LI. Synthesis and fluorescence behavior of 2,5-diphenyl-1,3,4-oxadiazole-containing bismaleimides and bissuccinimides[J]. Front Chem Sci Eng, 2013, 7(4): 381-387.

URL:

https://academic.hep.com.cn/fcse/EN/10.1007/s11705-013-1359-9
https://academic.hep.com.cn/fcse/EN/Y2013/V7/I4/381

Fig.1 Bismaleimides bearing 2,5-diphenyl-1,3,4-oxadiazole chromophores at , , position

Fig.2 Saturated bissuccinimides bearing 2,5-diphenyl-1, 3, 4-oxadiazole chromophores at and position

Fig.3 Synthetic strategies for maleimides bearing chromophores

Fig.4 Representative synthetic route toward Reagents and conditions: (i) polyphosphoric acid /NHNHHO, 130°C, 6 h; (ii) Fe, HCl, 50% CHOH, reflux; (iii) acetone, maleic anhydride, 50°C; (iv) acetic anhydride, AcONa, 80°C, 10 h

Fig.5 UV-vis absorption and fluorescence spectra of , , bismaleimides and saturated , bissuccinimides in 1,2-dichloroethane. Concentration: 3.0 × 10 mol?L

Tab.1 UV-vis absorption maxima (), extinction coefficient (), fluorescence emission maxima (), fluorescence quantum yields () and lifetimes () as well as the goodness-of-fit parameters () in 1,2-dichloroethane

Tab.2 Absorption and emission data and Stokes’ shifts (? = - ) of saturated model compound bissuccinimide in 1,2-dichloroethane (DCE), dichloromethane (DCM), , -dimethyforamine (DMF), acetonitrile (AN), methanol (MeOH), solvent parameter f= [( - 1)/(2 + 1)]/[( - 1)/(2 + 1)]

Fig.6 Fluorescence decay of saturated bissuccinimide in 1,2-dichloroethane, = 285 nm, λ = 335 nm, and the residues between the fit and experimental data. Concentration: 5.0 × 10 mol?L. Time interval between adjacent data points was 48 ps

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