Portal de Periódicos da CAPES

Polyfluorenes with on‐chain dibenzoborole units—Synthesis and anion‐induced photoluminescence quenching

2008; Wiley; Volume: 46; Issue: 8 Linguagem: Inglês

10.1002/pola.22610

1099-0518

Vasco D. B. Bonifácio, Jorge Morgado, Ullrich Scherf,

Organoboron and organosilicon chemistry

Journal of Polymer Science Part A: Polymer ChemistryVolume 46, Issue 8 p. 2878-2883 Rapid Communication Polyfluorenes with on-chain dibenzoborole units—Synthesis and anion-induced photoluminescence quenching Vasco D. B. Bonifácio, Corresponding Author Vasco D. B. Bonifácio vasco. [email protected] Macromolecular Chemistry Group, University of Wuppertal, Gaußstraße 20, D-42119 Wuppertal, Germany Instituto Superior Técnico, Departamento de Eng. Química e Biológica, Av. Rovisco Pais, 1049-001 Lisboa, PortugalMacromolecular Chemistry Group, University of Wuppertal, Gaußstraße 20, D-42119 Wuppertal, GermanySearch for more papers by this authorJorge Morgado, Jorge Morgado Instituto Superior Técnico, Departamento de Eng. Química e Biológica, Av. Rovisco Pais, 1049-001 Lisboa, Portugal Instituto de Telecomunicações, Instituto Superior Técnico, Av. Rovisco Pais, 1049-001 Lisboa, PortugalSearch for more papers by this authorUllrich Scherf, Ullrich Scherf Macromolecular Chemistry Group, University of Wuppertal, Gaußstraße 20, D-42119 Wuppertal, GermanySearch for more papers by this author Vasco D. B. Bonifácio, Corresponding Author Vasco D. B. Bonifácio vasco. [email protected] Macromolecular Chemistry Group, University of Wuppertal, Gaußstraße 20, D-42119 Wuppertal, Germany Instituto Superior Técnico, Departamento de Eng. Química e Biológica, Av. Rovisco Pais, 1049-001 Lisboa, PortugalMacromolecular Chemistry Group, University of Wuppertal, Gaußstraße 20, D-42119 Wuppertal, GermanySearch for more papers by this authorJorge Morgado, Jorge Morgado Instituto Superior Técnico, Departamento de Eng. Química e Biológica, Av. Rovisco Pais, 1049-001 Lisboa, Portugal Instituto de Telecomunicações, Instituto Superior Técnico, Av. Rovisco Pais, 1049-001 Lisboa, PortugalSearch for more papers by this authorUllrich Scherf, Ullrich Scherf Macromolecular Chemistry Group, University of Wuppertal, Gaußstraße 20, D-42119 Wuppertal, GermanySearch for more papers by this author First published: 18 March 2008 https://doi.org/10.1002/pola.22610Citations: 74Read the full textAboutPDF ToolsRequest permissionExport citationAdd to favoritesTrack citation ShareShare Give accessShare full text accessShare full-text accessPlease review our Terms and Conditions of Use and check box below to share full-text version of article.I have read and accept the Wiley Online Library Terms and Conditions of UseShareable LinkUse the link below to share a full-text version of this article with your friends and colleagues. Learn more.Copy URL Share a linkShare onEmailFacebookTwitterLinkedInRedditWechat Graphical Abstract The photoluminescence response of a novel, random 9,9-dialkylfluorene/dibenzoborole copolymer toward a series of nine inorganic anions was studied both in solution and in thin films. Photoluminescence quenching with sensitivity in the micromolar range was observed for fluoride, cyanide, and iodide. Hereby, the interaction of the copolymer with fluoride/cyanide or iodide follows different quenching mechanisms. Such copolymers are promising solid-state anion sensors. [Color figure can be viewed in the online issue, which is available at www.interscience.wiley.com.] REFERENCES AND NOTES 1 Thomas, S. W.,III;Joly, D.;Swager, T. M. Chem Rev 2007, 107, 1339–1386. 2Toxicity data for selected nerve agents: LCt 50 (inhalation mg · min/m3) Sarin (100), Soman (50), Tabum (200); LC 50 (mg/individual) Sarin (1700), Soman (300), Tabum (400). Sadik, O. A.;Land, W. H.,Jr.;Wang, J. Electroanalysis 2003, 15, 1149–1159. 3For 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; (b) Gupta, R. C.;Patterson, G. T.;Dettbarn, W. D. Toxicology 1987, 46, 329–341. 5 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. 6For examples of fluoride chemosensors, see: (a) Yamaguchi, S.;Akiyama, S.;Tamao, K. J Am Chem Soc 2001, 123, 11372–11375; (b) Yamaguchi, S.;Akiyama, S.;Tamao, K. J Organomet Chem 2002, 652, 3–9; (c) Kubo, Y.;Yamamoto, M.;Ikeda, M.;Takeuchi, M.;Shinkai, S.;Yamaguchi, S.;Tamao, K. Angew Chem Int Ed Engl 2003, 42, 2036–2040; (d) Solé, S.;Gabbaï, F. P. Chem Commun 2004, 1284–1285; (e) Melaimi, M.;Gabbaï, F. P. J Am Chem Soc 2005, 127, 9680–9681; (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; (g) Neumann, T.;Dienes, Y.;Baumgartner, T. Org Lett 2006, 8, 495–497; (h) Zhou, Z.;Xiao, S.;Xu, J.;Liu, Z.;Shi, M.;Li, F.;Yi, T.;Huang, C. Org Lett 2006, 8, 3911–3914; (i) Hudnall, T. W.;Melaimi, M.;Gabbaï, F. P. Org Lett 2006, 8, 2747–2749; (j) Liu, X. Y.;Bai, D. R.;Wang, S. Angew Chem Int Ed 2006, 45, 5475–5478; (l) Lee, M. H.;Gabbaï, F. P. Inorg Chem 2007, 46, 8132–8138; (m) Oehlke, A.;Auer, A. A.;Jahre, I.;Walfort, B.;Ruffer, T.;Zoufala, P.;Lang, H.;Spange, S. J Org Chem 2007, 72, 4328–4339. 7 Miyata, M.;Chujo, Y. Polym J 2002, 34, 967–969. For reviews in boron-containing polymers see: (a) Jäkle, F. Coord Chem Rev 2006, 250, 1107–1121; (b) Entwistle, C. D.;Marder, T. B. Chem Mater 2004, 16, 4574–4585; (c) Entwistle, C. D.;Marder, T. B. Angew Chem Int Ed 2002, 41, 2927–2931. 8The 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. 9 Asawapirom, U.;Güntner, R.;Forster, M.;Farrell, T.;Scherf, U. Synthesis 2002, 9, 1136–1142. 10 Chan, K. L.;McKiernan, M.;Towns, C.;Holmes, A. B. J Am Chem Soc 2005, 127, 7662–7663. 11(a) Dibenzoborole C12F8BC6F5 was obtained in 44% yield using a boron-tin exchange reaction. Attempts to prepare the compound from the lithiated biphenyl followed by the addition of Cl2B(C6F5) failed. Chase, P. A.;Piers, W. E.;Patrick, B. O. J Am Chem Soc 2000, 122, 12911–12912; 12 (b) 9-Phenyl-borafluorene was prepared in 55% yield, heating 2-biphenylyldiphenylborane at 300 °C. Köster, V.;Benedikt, G. Angew Chem Int Ed Engl 1963, 2, 323–324. 12Cyanide was reported to be a π-acceptor comparable in strength to the dimesitylboryl [B(mes)2] group. Shultz, A.;Kaim, W. Chem Ber 1989, 122, 1863–1868. After 6 months of storage, at room temperature under atmospheric conditions no changes in the 11B NMR spectrum of BPFO-10 were observed. 13In the synthesis of dibenzoboroles using TipB(OMe)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. 14Fluoride-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. 15 (a) Cyanide quenching was recently observed. Parab, K.;Venkatasubbaiah, K.;Jäkle, F. J Am Chem Soc 2006, 128, 12879–12885; (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; (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. 16 A slight emission enhancement of BPFO-10 in the presence of bromide was observed in solution. Citing Literature Volume46, Issue815 April 2008Pages 2878-2883 ReferencesRelatedInformation