Fluorene oligomer with tetrathiafulvalenes as pendant groups: Synthesis, electrochemical and spectroscopic properties

Polymer Bulletin

Volumn 63, Issue 6, 2009, Pages 815-827

  Zhang, Xue Chao ^a   Zhang, Yu ^a   Wang, Cheng Yun ^a   Lai, Guo Qiao ^b   Zhang, Lei ^a   Shen, Yong Jia ^a  

^a EAST CHINA UNIVERSITY OF SCIENCE AND TECHNOLOGY   (China)

^b HANGZHOU NORMAL UNIVERSITY   (China)

Author keywords

Charge transfer; Conducting materials; Fluorene; Fluorescence switch; TTF

Indexed keywords

CHAIN PROPAGATION; CHEMICAL OXIDATION; CONDUCTING MATERIALS; ELECTROACTIVE; FLUORENE MOIETY; FLUORENES; FLUORESCENCE INTENSITIES; FLUORESCENCE SPECTRA; FLUORESCENCE SWITCH; INTERNAL CHARGE TRANSFER; INTRAMOLECULAR INTERACTIONS; PENDANT GROUPS; PHOTO-INDUCED ELECTRON TRANSFER; SPECTROSCOPIC PROPERTY; TETRATHIAFULVALENES; YAMAMOTO COUPLING;

CHARGE TRANSFER; CHEMICAL BONDS; CHEMICAL OXYGEN DEMAND; CYCLIC VOLTAMMETRY; ELECTROCHEMICAL PROPERTIES; ELECTRON TRANSITIONS; ENERGY TRANSFER; FLUORINE CONTAINING POLYMERS; ION EXCHANGE; MASS TRANSFER; SULFUR COMPOUNDS; SWITCHES; SYNTHESIS (CHEMICAL);

FLUORESCENCE;

EID: 72149102104     PISSN: 01700839     EISSN: None     Source Type: Journal    
DOI: 10.1007/s00289-009-0122-3     Document Type: Article

References (34)

1. ML Sun QL Niu RQ Yang B Du RS Liu W Yang JB Peng Y Cao 2007 Fluorene-based copolymers for color-stable blue light-emitting diodes Eur Polym J 43 1916 1922 10.1016/j.eurpolymj.2007.02.008 1:CAS:528:DC%2BD2sXkvF2nt7g%3D (Pubitemid 46660849)
2. M Fukuda K Sawada K Yoshino 1993 Synthesis of fusible and soluble conducting polyfluorene derivatives and their characteristics J Polym Sci A 31 2465 2471 10.1002/pola.1993.080311006 1:CAS:528:DyaK3sXmt1Kmsbo%3D (Pubitemid 23708024)
3. ZJ Zhao XJ Xu F Wang G Yu P Lu YQ Liu DB Zhu 2006 Synthesis and characterization of light-emitting materials composed of carbazole, pyrene and fluorene Synth Met 156 209 214 10.1016/j.synthmet.2005.11.011 1:CAS:528:DC%2BD28XhslymtLg%3D (Pubitemid 43290168)
4. HP Rathnayake A Cirpan PM Lahti FE Karasz 2006 Optimizing LED properties of 2,7-bis(phenylethenyl)fluorenes Chem Mater 18 560 566 10.1021/cm052144o 1:CAS:528:DC%2BD2MXhtlensrjN (Pubitemid 43293330)
5. SH Lee T Nakamura T Tsutsui 2001 Synthesis and characterization of oligo(9,9-dihexyl-2,7-fluorene ethynylene)s: for application as blue light-emitting diode Org Lett 3 2005 2007 10.1021/ol010069r 1:CAS:528: DC%2BD3MXjvVWit7o%3D (Pubitemid 33631700)
6. J Yang CY Jiang Y Zhang RQ Yang W Yang Q Hou Y Cao 2004 High-efficiency saturated red emitting polymers derived from fluorene and naphthoselenadiazole Macromolecules 37 1211 1218 10.1021/ma035743u 1:CAS:528:DC%2BD2cXjs1antg%3D%3D
7. XW Zhan YQ Liu DB Zhu WT Huang QH Gong 2001 Large femtosecond third-order nonlinear optical response in a novel donor-acceptor copolymer consisting of ethynylfluorene and tetraphenyldiaminobiphenyl units Chem Mater 13 1540 1544 10.1021/cm000961c 1:CAS:528:DC%2BD3MXitlegsrk%3D
8. KD Belfield KJ Schafer W Mourad BA Reinhardt 2000 Synthesis of new two-photon absorbing fluorene derivatives via Cu-mediated ullmann condensations J Org Chem 65 4475 4481 10.1021/jo991950+ 1:CAS:528:DC%2BD3cXkt1GrtLY%3D (Pubitemid 30620552)
9. XH Zhou JC Yan J Pei 2004 Exploiting an imidazole-functionalized polyfluorene derivative as a chemosensory material Macromolecules 37 7078 7080 10.1021/ma049057m 1:CAS:528:DC%2BD2cXms1OlsL4%3D
10. F Larmat JR Reynolds BA Reinhardt LL Brott SJ Clarson 1997 Comparative reactivity of thiophene and 3,4-(ethylenedioxy)thiophene as terminal electropolymerizable units in bis-heterocycle arylenes J Polym Sci A 35 3627 3636 10.1002/(SICI)1099-0518(199712)35:17<3627::AID-POLA2>3.0.CO;2-P 1:CAS:528:DyaK2sXntlCrt70%3D
11. B Liu BS Gaylord S Wang GC Bazan 2003 Effect of chromophore-charge distance on the energy transfer properties of water-soluble conjugated oligomers J Am Chem Soc 125 6705 6714 10.1021/ja028961w 1:CAS:528:DC%2BD3sXjs1Glt7g%3D (Pubitemid 36667454)
12. CH Xue VR Donuru HY Liu 2006 Facile, versatile prepolymerization and postpolymerization functionalization approaches for well-defined fluorescent conjugated fluorene-based glycopolymers Macromolecules 39 5747 5752 10.1021/ma060422e 1:CAS:528:DC%2BD28XnsV2htrw%3D (Pubitemid 44366473)
13. MR Bryce 2000 Functionalised tetrathiafulvalenes: new applications as versatile π-electron systems in materials chemistry J Mater Chem 10 589 598 10.1039/a908385e 1:CAS:528:DC%2BD3cXhtlegurg%3D
14. Farges JP (1994) Organic conductors: fundamentals and applications. Marcel Dekker, New York
15. SG Liu HY Liu K Bandyopadhyay ZQ Gao L Echegoyen 2000 Dithia-crown-annelated tetrathiafulvalene disulfides: synthesis electrochemistry, self-assembled films, and metal ion recognition J Org Chem 65 3292 3298 10.1021/jo000115l 1:CAS:528:DC%2BD3cXitl2jsrY%3D (Pubitemid 30346779)
16. TK Hansen T Jorgensen PC Stein J Becher 1992 Crown ether derivatives of tetrathiafulvalene 1 J Org Chem 57 6403 6409 10.1021/jo00050a010 1:CAS:528:DyaK3sXit1aitQ%3D%3D
17. 2+ by a modified surface incorporating a TTF-based redox-switchable ligand J Am Chem Soc 126 12194 12195 10.1021/ja047411q 1:CAS:528:DC%2BD2cXntlOjtr8%3D (Pubitemid 39304864)
18. KA Nielsen JO Jeppesen E Levillain J Becher 2003 Mono-tetrathiafulvalene calix[4]pyrrole in the electrochemical sensing of anions Angew Chem Int Ed 42 187 191 10.1002/anie.200390074 1:CAS:528:DC%2BD3sXos1altg%3D%3D (Pubitemid 36131066)
19. 60, mimicking the performance of an AND logic gate J Org Chem 71 3970 3972 10.1021/jo052494u 1:CAS:528:DC%2BD28Xjtleqt7c%3D
20. HC Li JO Jeppesen E Levillain J Becher 2003 A mono-TTF-annulated porphyrin as a fluorescence switch Chem Commun 7 846 847 10.1039/b212456d
21. S Leroy-Lhez J Baffreau L Perrin E Levillain M Allain MJ Blesa P Hudhomme 2005 Tetrathiafulvalene in a perylene-3,4:9,10-bis(dicarboximide)-based dyad: a new reversible fluorescence-redox dependent molecular system J Org Chem 70 6313 6320 10.1021/jo050766n 1:CAS:528:DC%2BD2MXls1Ogurc%3D (Pubitemid 41076515)
22. GX Zhang DQ Zhang XF Guo DB Zhu 2004 A new redox-fluorescence switch based on a triad with tetrathiafulvalene and anthracene units Org Lett 6 1209 1212 10.1021/ol036511i 1:CAS:528:DC%2BD2cXitValsbc%3D (Pubitemid 38692025)
23. L Huchet S Akoudad J Roncali 1998 Electrosynthesis of highly electroactive tetrathiafulvalene-derivatized polythiophenes Adv Mater 10 541 545 10.1002/(SICI)1521-4095(199805)10:7<541::AID-ADMA541>3.0.CO;2-1 1:CAS:528:DyaK1cXjt1egt7g%3D
24. PJ Skabara R Berridge EJ McInnes DP West SJ Coles MB Hursthouse K Müllen 2004 The electroactivity of tetrathiafulvalene vs. polythiophene: synthesis and characterization of a fused thieno-TTF polymer J Mater Chem 14 1964 1969 10.1039/b400809j 1:CAS:528:DC%2BD2cXlt1alsbw%3D
25. Beeby A, Bryce MR, Christensen CA, Cooke G, Duclairoir FM, Rotello VM (2002) Electrochemically controlled interactions between TTF-based dendrimers and an electron-rich oligomer. Chem Commun 2950-2951
26. G Zhou G Qian L Ma YX Cheng ZY Xie LX Wang XB Jing F Wang 2005 Polyfluorenes with phosphonate groups in the side chains as chemosensors and electroluminescent materials Macromolecules 38 5416 5424 10.1021/ma050807h 1:CAS:528:DC%2BD2MXksVOrs74%3D (Pubitemid 41028109)
27. N Svenstrup KM Rasmussen TK Hansen J Becher 1994 The chemistry of TTFTT; 1: new efficient synthesis and reactions of tetrathiafulvalene-2,3,6,7- tetrathiolate (TTFTT): an important building block in TTF-system Synthesis 8 809 812 10.1055/s-1994-25580
28. CA Christensen MR Bryce J Becher 2000 New multi(tetrathiafulvalene) dendrimers Synthesis 169 5 1704
29. SP Dudek M Pouderoijen R Abbel AP Schenning EW Meijer 2005 Synthesis and energy-transfer properties of hydrogen-bonded oligofluorenes J Am Chem Soc 127 11763 11768 10.1021/ja052054k 1:CAS:528:DC%2BD2MXms1Kmsrk%3D (Pubitemid 41208762)
30. Y Zhang LZ Cai CY Wang GQ Lai YJ Shen 2008 Synthesis and properties of a tetrathiafulvalene-perylene tetracarboxylic diimide-tetrathiafulvalene dyad New J Chem 32 1968 1973 10.1039/b719844b 1:CAS:528:DC%2BD1cXhtlaqsbfI
31. GX Zhang DQ Zhang XF Guo DB Zhu 2002 A new redox-fluorescence switch based on a triad with tetrathiafulvalene and anthracene units Org Lett 6 1209 1212 10.1021/ol036511i
32. C Farren CA Christensen S FitzGerald MR Bryce A Beeby 2002 Synthesis of novel phthalocyanine-tetrathiafulvalene hybrids; intramolecular fluorescence quenching related to molecular geometry J Org Chem 67 9130 9139 10.1021/jo020340y 1:CAS:528:DC%2BD38XovFSktLc%3D (Pubitemid 36040352)
33. S Frenzel S Arndt R Ma K Müllen 1995 Synthesis of tetrathiafulvalene polymers J Mater Chem 10 1529 1537 10.1039/jm9950501529
34. YB Liu CY Wang MJ Li GQ Lai YJ Shen 2008 Synthesis and spectroscopic and electrochemical properties of TTF-derivatized polycarbazole Macromolecules 41 2045 2048 10.1021/ma702035c 1:CAS:528:DC%2BD1cXitVyisbw%3D