RESEARCH ARTICLE

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

  • Xin ZHANG , 1 ,
  • Zichen LI 2
Expand
  • 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

Received date: 01 Oct 2013

Accepted date: 02 Nov 2013

Published date: 05 Dec 2013

Copyright

2014 Higher Education Press and Springer-Verlag Berlin Heidelberg

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.

Cite this article

Xin ZHANG , Zichen LI . Synthesis and fluorescence behavior of 2,5-diphenyl-1,3,4-oxadiazole-containing bismaleimides and bissuccinimides[J]. Frontiers of Chemical Science and Engineering, 2013 , 7(4) : 381 -387 . DOI: 10.1007/s11705-013-1359-9

Acknowledgments

We thank the Alexander von Humboldt Foundation and Mrs. Elisabeth, and Dr. Georg Krohne for their kind help.
Supporting information for this article is available free of charge via the Internet.
1
Gandini A. The furan/maleimide Diels-Alder reaction: A versatile click–unclick tool in macro molecular synthesis. Progress in Polymer Science, 2013, 38(1): 1–29

DOI

2
Warman J M, Abellon R D, Verhey H J, Verboeven J W, Hofstraat J W. Maleimido-fluoroprobe: A dual-purpose fluorogenic probe of polymerization dynamics. Journal of Physical Chemistry B, 1997, 101(25): 4913–4916

DOI

3
Zhang X, Li Z C, Li K B, Lin S, Du F S, Li F M. Donor/acceptor vinyl monomers and their polymers: synthesis, photochemical and photophysical behavior. Progress in Polymer Science, 2006, 31(10): 893–948

DOI

4
Broyer R M, Grover G N, Maynard H D. Emerging synthetic approaches for protein-polymer conjugations. Chemical Communications, 2011, 47(8): 2212–2226

DOI

5
Wang B B, Zhang X, Jia X R, Li Z C, Ji Y, Yang L, Wei Y. Fluorescence and aggregation behavior of poly(amidoamine) dendrimers peripherally modified with aromatic chromophores: The effect of dendritic architectures. Journal of the American Chemical Society, 2004, 126(46): 15180–15194

DOI

6
Sahoo M K, Mhaske S B, Argade N P. Facile routes to alkoxymaleimides/maleic anhydrides. Synthesis, 2003, 7(4): 346–349

7
Corrie J E T, Munasinghe V R N, Rettig W. Synthesis and fluorescence properties of substituted 7-aminocoumarin-3-carboxylate derivatives. Journal of Heterocyclic Chemistry, 2000, 37(6): 1447–1455

DOI

8
Wu H P, Aumann R, Frohlich R, Wibbeling B, Kataeva O. Highly selective formation of [4+2] and [4+3] cycloadducts of tetrahydroindenes generated in situ from a (1-alkynyl)carbene tungsten complex by the metalla-1,3,5-hexatriene route. Chemistry (Weinheim an der Bergstrasse, Germany), 2001, 7(23): 5084–5093

DOI

9
Gousse C, Gandini A. Diels–Alder polymerization of difurans with bismaleimides. Polymer International, 1999, 48(8): 723–731

DOI

10
Nicolaou K C, Zhong Y L, Baran P S, Jung J, Choi H S, Yoon W H. Completion and synthesis of advanced analogs. Journal of the American Chemical Society, 2002, 124(10): 2202–2211

DOI

11
Zhang X, Li Z C, Li K B, Du F S, Li F M. Multi-maleimides bearing electron-donating chromophores: Reversible fluorescence and aggregation behavior. Journal of the American Chemical Society, 2004, 126(39): 12200–12201

DOI

12
Du F S, Li Z C, Li F M. Vinyl monomers bearing chromophore moieties and their polymers. VIII. Synthesis and fluorescence behavior of a vinyloxy monomer having an electron-accepting chromophore moiety, p-((vinyloxy)methyl)benzonitrile, and its polymers. Journal of Polymer Science. Part A, Polymer Chemistry, 1999, 37(2): 179–187

DOI

13
Tanaka F, Thayumanavan R, Barbas C F. Fluorescent detection of carbon–carbon bond formation. Journal of the American Chemical Society, 2003, 125(28): 8523–8528

DOI

14
Girouard S, Houle M H, Grandbois A, Keillor J W, Michnick S W. Synthesis and characterization of dimaleimide fluorogens designed for specific labeling of proteins. Journal of the American Chemical Society, 2005, 127(2): 559–566

DOI

15
Miller C W, Jonsson E S, Hoyle C E, Viswanathan K, Valente E J. Evaluation of N-aromatic maleimides as free radical photoinitiators: A photophysical and photopolymerization characterization. Journal of Physical Chemistry B, 2001, 105(14): 2707–2717

DOI

16
Trost B M, Kallander L S. A versatile enantioselective strategy toward L-C-nucleosides: A total synthesis of L-Showdomycin. Journal of Organic Chemistry, 1999, 64(15): 5427–5435

DOI

17
Cheng S H, Hsiao S H, Su T H, Liou G S. Novel aromatic poly(amine-imide)s bearing a pendent triphenylamine group: synthesis, thermal, photophysical, electrochemical, and electrochromic characteristics. Macromolecules, 2005, 38(2): 307–316

DOI

18
Wang C, Zhang C, Wang P, Zhu P, Wu W, Ye C, Dalton L R. High Tg donor-embedded polyimides for second-order nonlinear optical applications. Polymer, 2000, 41(7): 2583–2590

DOI

19
Saegusa Y, Koshikawa T, Nakamura S. Synthesis and characterization of 1,3,4-oxadiazole-containing polyazomethines. Journal of Polymer Science. Part A, Polymer Chemistry, 1992, 30(7): 1369–1373

DOI

20
Reddy P Y, Kondo S, Fujita S, Toru T. Efficient synthesis of fluorophore-linked maleimide derivatives. Synthesis, 1998, 8(9): 999–1002

DOI

21
Conley N R, Hung R J, Willson C G. A new synthetic route to authentic N-substituted aminomaleimides. Journal of Organic Chemistry, 2005, 70(11): 4553–4555

DOI

22
Fruk L, Graham D. The electronic effects on the formation of N-arylmaleimides and isomaleimides. Heterocycles, 2003, 60(10): 2305–2313

DOI

23
Ivanov D, Constantinescu M. Computational study of maleamic acid cyclodehydration. Journal of Physical Organic Chemistry, 2003, 16(6): 348–354

DOI

24
Chihab-Eddine A, Daich A, Jilale A, Decroix B. Synthesis and reactivity of (1S)-N-(1-phenylethyl) maleimide towards nucleophiles: An application to preparation of chiral pyrroloisothiochroman and pyrrolobenzo[d]thiepine based on pi-cationic cyclization. Tetrahedron Letters, 2001, 42(4): 573–576

DOI

25
Clevenger R C, Turnbull K D. Synthesis on N-alkylated maleimides. Synthetic Communications, 2000, 30(8): 1379–1388

DOI

26
Berson J A, Swidler R A. Synthesis of maleimide. Journal of the American Chemical Society, 1954, 76(10): 2835–2836

DOI

27
Hattemer E, Zentel R, Mecher E, Meerholz K. Synthesis and characterization of novel multifunctional high-Tg photorefractive materials obtained via reactive precursor polymers. Macromolecules, 2000, 33(6): 1972–1977

DOI

28
Aponte M A, Butler G B. Copolymers containing alternating sequences of nucleic acid-base pairs. I. Monomer synthesis. Journal of Polymer Science. Part A, Polymer Chemistry, 1984, 22(11): 2841–2858

DOI

29
Schwartz A L, Lerner L M. Synthesis and properties of N-(2,3,5-tri-O-acetyl-D-ribofuranosyl) maleimide. Journal of Organic Chemistry, 1975, 40(1): 24–28

DOI

30
King H D, Dubowchik G M, Walker M A. Walker, M. A. Facile synthesis of maleimide bifunctional linkers. Tetrahedron Letters, 2002, 43(11): 1987–1990

DOI

31
Walker M A. A high yielding synthesis of N-alkyl maleimides using a novel modification of the Mitsunobu reaction. Journal of Organic Chemistry, 1995, 60(16): 5352–5355

DOI

32
Berlin Y A, Hutchison G R, Rempala P, Ratner M A, Michl J. Charge hopping in molecular wires as a sequence of electron-transfer reactions. Journal of Physical Chemistry A, 2003, 107(19): 3970–3980

DOI

33
Mataga N, Kaifu Y, Koizumi M. Solvent effects upon fluorescence spectra and the dipole moments of excited molecules. Bulletin of the Chemical Society of Japan, 1956, 29(4): 465–470

DOI

34
Von Lippert E Z. Spektroskopische Bestimmung des Dipolmomentes Aromatischer Verbin- dungen im Ersten Angeregten Singuletzustand. Electrochemistry, 1957, 61(9): 962–975

35
Lakowicz J R. Principles of Fluorescence Spectroscopy, 2nd ed. Plenum Press: New York, 1999, 192

36
Kanaoka Y, Machida M, Ando K, Sekine T. N-(1-Anilinonaphthyl-4)maleimide: A fluorescent hydrophobic probe directed to thiol groups in protein. Biochimica et Biophysica Acta, 1970, 207(1): 269–277

DOI

37
Verhey H J, Bekker C H W, Verhoeven J W, Hofstraat J W. A fluorogenic charge-transfer polarity probe for the derivatisation of thiols and amines. New Journal of Chemistry, 1996, 20(7-8): 809–814

Outlines

/