Polyfluorenes with on-chain dibenzoborole units-synthesis and anion-induced photoluminescence quenching

Journal of Polymer Science, Part A: Polymer Chemistry

Volumn 46, Issue 8, 2008, Pages 2878-2883

  Bonifácio, Vasco D B ^a,b   Morgado, Jorge ^b   Scherf, Ullrich ^a  

^a UNIVERSITY OF WUPPERTAL   (Germany)

^b INSTITUTO SUPERIOR TÉCNICO   (Portugal)

Author keywords

Conjugated polymers; Dibenzoborole building blocks; Fluorescence; Sensors

Indexed keywords

CYANIDES; FLUORESCENCE; GASES; SENSORS; TOXIC MATERIALS;

DIBENZOBOROLE BUILDING BLOCKS; TOXIC GASES;

CONJUGATED POLYMERS;

EID: 41749107364     PISSN: 0887624X     EISSN: 10990518     Source Type: Journal    
DOI: 10.1002/pola.22610     Document Type: Article

References (35)

1. Thomas, S. W., III; Joly, D.; Swager, T. M. Chem Rev 2007, 107, 1339-1386.
2. 50 (mg/individual) Sarin (1700), Soman (300), Tabum (400). Sadik, O. A.; Land, W. H., Jr.; Wang, J. Electroanalysis 2003, 15, 1149-1159.
3. For a recent review on chromogenic and fluorogenic reagents for chemical warfare nerve agents' detection see: Royo, S.; Martínez- Máñez, R.; Sancenón, F.; Costero, A. M.; Parra, M.; Gil, S. Chem Commun 2007, 4839-4847.
4. (a) Xie, Y.; Popov, B. N. Anal Chem 2000, 72, 2075-2079;
5. (b) Gupta, R. O.; Patterson, G. T.; Dettbarn, W. D. Toxicology 1987, 46, 329-341.
6. The WHO guideline values for fluorine and cyanide in drinking waters are 1.5 ppm (78 μM) and 0.07 ppm (2.69 μM), respectively; World Health Organization. Guidelines for Drinking-Water Quality, 3rd ed.; World Health Organization: Geneva, 2006.
7. For examples of fluoride chemosensors, see: (a) Yamaguchi, S.; Akiyama, S.; Tamao, K. J Am Chem Soc 2001, 123, 11372-11375;
8. (b) Yamaguchi, S.; Akiyama, S.; Tamao, K. J Organomet Chem 2002, 652, 3-9;
9. (c) Kubo, Y.; Yamamoto, M.; Ikeda, M.; Takeuchi, M.; Shinkai, S.; Yamaguchi, S.; Tamao, K. Angew Chem Int Ed Engl 2003, 42, 2036-2040;
10. (d) Solé, S.; Gabbaï, F. P. Chem Commun 2004, 1284-1285;
11. (e) Melaimi, M.; Gabbaï, F. P. J Am Chem Soc 2005, 127, 9680-9681;
12. (f) Liu, Z.-Q.; Shi, M.; Li, F.-Y.; Fang, Q.; Chen, Z.-H.; Yi, T.; Huang, C.-H. Org Lett 2005, 7, 5481-5484;
13. (g) Neumann, T.; Dienes, Y.; Baumgartner, T. Org Lett 2006, 8, 495-497;
14. (h) Zhou, Z.; Xiao, S.; Xu, J.; Liu, Z.; Shi, M.; Li, F.; Yi, T.; Huang, C. Org Lett 2006, 8, 3911-3914;
15. (i) Hudnall, T. W; Melaimi, M.; Gabbaï, F. P. Org Lett 2006, 8, 2747-2749;
16. (j) Liu, X. Y.; Bai, D. R.; Wang, S. Angew Chem Int Ed 2006, 45, 5475-5478;
17. (l) Lee, M. H.; Gabbaï, F. P. Inorg Chem 2007, 46, 8132-8138;
18. (m) Oehlke, A.; Auer, A. A.; Jahre, L; Walfort, B.; Ruffer, T.; Zoufala, P.; Lang, H.; Spange, S. J Org Chem 2007, 72, 4328-4339.
19. Miyata, M.; Chujo, Y Polym J 2002, 34, 967-969.
20. For reviews in boron-containing polymers see: (a) Jäkle, E Coord Chem Rev 2006, 250, 1107-1121;
21. (b) Entwistle, C. D.; Marder, T. B. Chem Mater 2004, 16, 4574-4585;
22. (c) Entwistle, C. D.; Marder, T. B. Angew Chem Int Ed 2002, 41, 2927-2931.
23. The synthesis of poly(aryleneethynylene)s containing protected diarylboryl side chains [bis (4-hexyl-2,6-dimethylphenyl)boryl] was recently published. Sun, Y.; Ross, N.; Zhao, S.-B.; Huszarik, K; Jia, W.-L.; Wang, R.-Y; Macartney, D.; Wang, S. J Am Chem Soc 2007, 129, 7510-7511.
24. Asawapirom, U.; Güntner, R.; Forster, M.; Farrell, T.; Scherf, U. Synthesis 2002, 9, 1136-1142.
25. Chan, K. L.; McKiernan, M.; Towns, C.; Holmes, A. B. J Am Chem Soc 2005, 127, 7662-7663.
26. 5) failed. Chase, P. A.; Piers, W. E.; Patrick, B. O. J Am Chem Soc 2000, 122, 12911-12912;
27. (b) 9-Phenyl-borafluorene was prepared in 55% yield, heating 2-biphenylyldiphenylborane at 300°C. Koster, V; Benedikt, G. Angew Chem Int Ed Engl 1963, 2, 323-324.
28. 11B NMR spectrum of BPFO-10 were observed.
29. 2 (ortho-isopropyl protection) a yield of 38% was obtained. Yamaguchi, S.; Shirasaka, T; Akiyama, S.; Tamao, K. J Am Chem Soc 2002, 124, 8816-8817.
30. Fluoride-mediated photoluminescence quenching in polysilanes was reported to be sensitive to long alkyl groups attached to the silicon atoms. Kwak, G.; Fujiki, M.; Masuda, T. Macromolecules 2004, 37, 2422-2426.
31. (a) Cyanide quenching was recently observed.- c
32. Parab, K.; Venkatasubbaiah, K.; Jäkle, F. J Am Chem Soc 2006, 128, 12879-12885;
33. (b) For the synthesis of cyanide-sensitive fluorescent probes based on boronic acids see: Badugu, R.; Lakowicz, J. R.; Geddes, C. D. Dyes Pigment 2005, 64, 49-55;
34. (c) Boron-doped carbon nanotubes were recently postulated as potential cyanide sensors. Zhang, Y.; Zhang, D.; Liu, C. J Phys Chem B 2006, 110, 4671-4674.
35. A slight emission enhancement of BPFO-10 in the presence of bromide was observed in solution.