Tetrathiafulvalene (TTF)-based gelators: Stimuli responsive gels and conducting nanostructures

Science China Chemistry

Volumn 54, Issue 4, 2011, Pages 596-602

  Yang, Xingyuan ^a,b   Zhang, Deqing ^a   Zhang, Guanxin ^a   Zhu, Daoben ^a  

^a INSTITUTE OF CHEMISTRY   (China)

^b UNIVERSITY OF CHINESE ACADEMY OF SCIENCES   (China)

Author keywords

conducting nanostructures; gelator; gels; self assembly; tetrathiafulvalene

Indexed keywords

BUILDING BLOCKES; CONDUCTING MATERIALS; CONDUCTING NANOSTRUCTURES; ELECTRON DONORS; GELATION PROCESS; GELATOR; GELATORS; RECENT PROGRESS; STIMULI-RESPONSIVE; SWITCHABLE; TETRATHIAFULVALENES; TTF DERIVATIVES;

COAGULATION; GELATION; GELS; SELF ASSEMBLY;

NANOSTRUCTURES;

EID: 79954544017     PISSN: 16747291     EISSN: None     Source Type: Journal    
DOI: 10.1007/s11426-011-4225-y     Document Type: Review

References (40)

1. M. Narita C.U. Pittman 1976 Preparation of tetra-thialfulvalenes (TTF) and their selenium analogs-tetraselenafulvalenes (TSEF) Synthesis 8 489 514 10.1055/s-1976-24099
2. F. Wudl M.L. Kaplan 1974 A convenient synthesis of 1,4,5,8-tetrahydro-1, 4,5,8-tetrathiafulvalene J Org Chem 39 3608 3609 10.1021/jo00938a042 1:CAS:528:DyaE2MXhs1Ohsg%3D%3D
3. J. Ferraris D.O. Cowan V.V. Walatka J.H. Perlstein 1973 Electron transfer in a new highly conducting donor-acceptor complex J Am Chem Soc 95 948 949 10.1021/ja00784a066 1:CAS:528:DyaE3sXpslGhug%3D%3D
4. J.M. Fabre 2004 Synthesis strategies and chemistry of nonsymmetrically substituted tetrachalcogenafulvalenes Chem Rev 104 5133 5150 10.1021/cr0306440 1:CAS:528:DC%2BD2cXlvVart7k%3D
5. J. Yamada H. Akutsu 2004 New trends in the synthesis of π-electron donors for molecular conductors and superconductors Chem Rev 104 5057 5083 10.1021/cr0306687 1:CAS:528:DC%2BD2cXnt12gs78%3D
6. M. Fourmigué P. Batail 2004 Activation of hydrogen- and halogen-bonding interactions in tetrathiafulvalene-based crystalline molecular conductors Chem Rev 104 5379 5418 10.1021/cr030645s
7. J.O. Jeppesen M.B. Nielsen J. Becher 2004 Tetrathialfulvalene cyclophanes and cage molecules Chem Rev 104 5115 5131 10.1021/cr030630u 1:CAS:528:DC%2BD2cXoslSgsLs%3D
8. Canevet D, Sallé M, Zhang GX, Zhang DQ, Zhu DB. Tetrathiafulvalene (TTF) derivatives: Key building-blocks for switchable processes. Chem Commun, 2009, 2245-2269
9. N.N.P. Moonen A.H. Flood J.M. Fernández J.F. Stoddart 2005 Towards a rational design of molecular switches and sensors from their basic building blocks Top Curr Chem 262 99 132 10.1007/128-009 1:CAS:528:DC%2BD28XitVSlt7g%3D (Pubitemid 44420781)
10. E.R. Kay D.A. Leigh F. Zerbetto 2007 Synthetic molecular motors and mechanical machines Angew Chem Int Ed 46 72 191 10.1002/anie.200504313 1:CAS:528:DC%2BD2sXitlCqtQ%3D%3D (Pubitemid 46074791)
11. V. Balzani A. Credi M. Venturi 2009 Light powered molecular machines Chem Soc Rev 38 1542 1550 10.1039/b806328c 1:CAS:528:DC%2BD1MXmsVSms7c%3D
12. L. Fang M.A. Olson D. Benítez E. Tkatchouk W.A. Goddard III J.F. Stoddart 2010 Chem Soc Rev 39 17 29 10.1039/b917901a 1:CAS:528: DC%2BD1MXhsFGrsrvJ
13. C. Rovira 2004 Bis(ethylenethio)tetrathiafulvalene (BET-TTF) and related dissymmetrical electron donors: From the molecule to functional molecular materials and devices (OFETs) Chem Rev 104 5289 5317 10.1021/cr030663+ 1:CAS:528:DC%2BD2cXovFSmtb4%3D
14. M. Hasegawa M. Iyoda 2010 Conducting supramolecular nanofibers and nanorods Chem Soc Rev 39 2420 531 10.1039/b909347h 1:CAS:528: DC%2BC3cXnsl2rtLo%3D
15. P. Terech R.G. Weiss 1997 Low molecular mass gelators of organic liquids and the properties of their gels Chem Rev 97 3133 3159 10.1021/cr9700282 1:CAS:528:DyaK2sXnsFSitLk%3D (Pubitemid 127667409)
16. D. Abdallah R.G. Weiss 2000 Organogels and low molecular mass organic gelators Adv Mater 12 1237 1247 10.1002/1521-4095(200009)12:17<1237::AID- ADMA1237>3.0.CO;2-B 1:CAS:528:DC%2BD3cXnt1Wlurk%3D
17. Wang S, Shen W, Feng YL, Tian H. Effective enhancement of fluorescence signals in rotaxane-doped reversible hydrosol-gel systems. Chem Commun, 2006, 1497-1499
18. L.L. Zhu X. Ma F.Y. Ji Q.C. Wang H. Tian 2007 A multiple switching bisthienylethene and its photochromic fluorescent organogelator Chem Eur J 13 9216 9222 10.1002/chem.200700860 1:CAS:528:DC%2BD2sXhsVamsL3F (Pubitemid 350178586)
19. N.M. Sangeetha U. Maitra 2005 Supramolecular gels: Functions and uses Chem Soc Rev 34 821 836 10.1039/b417081b 1:CAS:528:DC%2BD2MXhtVWmurnK (Pubitemid 41472018)
20. M.O.M. Piepenbrock G.O. Lloyd N. Clarke J.W. Steed 2010 Metal- and anionbinding supramolecular gels Chem Rev 110 1960 2004 10.1021/cr9003067 1:CAS:528:DC%2BD1MXhsF2jsrfM
21. M. Jørgensen K. Bechgaard 1994 Synthesis and structural characterization of a bis-arborol-tetrathiafulvalene gel: Toward a self-assembling "molecular" wire J Org Chem 59 5877 5882 10.1021/jo00099a012
22. Gall TL, Pearson C, Bryce MR, Petty MC, Dahlgaard H, Becher J. Arborol-functionalised tetrathiafulvalene derivatives: Synthesis and thin-film formation. Eur J Org Chem, 2003, 3562-3568
23. C. Wang D.Q. Zhang D.B. Zhu 2005 A low-molecular-mass gelator with an electroactive tetrathiafulvalene group: Tuning the gel formation by charge-transfer interaction and oxidation J Am Chem Soc 127 16372 16373 10.1021/ja055800u 1:CAS:528:DC%2BD2MXhtFynurbM (Pubitemid 41740369)
24. C. Wang F. Sun D.Q. Zhang G.X. Zhang D.B. Zhu 2010 Cholesterol- substituted tetrathiafulvalene (TTF) compound: Formation of organogel and supramolecular chirality Chin J Chem 28 622 626 10.1002/cjoc.201090123 1:CAS:528:DC%2BC3cXmtlartbY%3D
25. C. Wang Q. Chen F. Sun D.Q. Zhang G.X. Zhang Y.Y. Huang R. Zhao D.B. Zhu 2010 Multistimuli responsive organogels based on a new gelator featuring tetrathiafulvalene and azobenzene groups: Reversible tuning of the gel-sol transition by redox reactions and light irradiation J Am Chem Soc 132 3092 3096 10.1021/ja910721s 1:CAS:528:DC%2BC3cXhvF2lu7g%3D
26. Y.L. Zhao I. Aprahamian A. Trabolsi N. Erina J.F. Stoddart 2008 Organogel formation by a cholesterol-stoppered bistable [2]rotaxane and its dumbbell precursor J Am Chem Soc 130 6348 6350 10.1021/ja800731k 1:CAS:528: DC%2BD1cXlt1Ggs7s%3D (Pubitemid 351706094)
27. X.Y. Yang G.X. Zhang D.Q. Zhang D.B. Zhu 2010 A new ex-TTF-based organogelator: Formation of organogels and tuning with fullerene Langmuir 26 11720 11725 10.1021/la101193z 1:CAS:528:DC%2BC3cXms1Sgsrg%3D
28. D.B. Amabilino J. PuigmartÍ-Luis 2010 Gels as a soft matter route to conducting nanostructured organic and composite materials Soft Matter 6 1605 1612 10.1039/b923618j 1:CAS:528:DC%2BC3cXksVGhtr0%3D
29. T. Kitamura S. Nakaso N. Mizoshita Y. Tochigi T. Shimomura M. Moriyama K. Ito T. Kato 2005 Electroactive supramolecular self-assembled fibers comprised of doped tetrathiafulvalene-based gelators J Am Chem Soc 127 14769 14775 10.1021/ja053496z 1:CAS:528:DC%2BD2MXhtVGis7%2FK (Pubitemid 41511015)
30. T. Kitahara M. Shirakawa S.I. Kawano U. Beginn N. Fujita S. Shinkai 2005 Creation of a mixed-valence state from one-dimensionally aligned TTF utilizing the self-assembling nature of a low molecular-weight gel J Am Chem Soc 127 14980 14981 10.1021/ja0552038 1:CAS:528:DC%2BD2MXhtVKhsb7E (Pubitemid 41547337)
31. J. Puigmartí-Luis V. Laukhin P. del Pino J. Vidal-Gancedo C. Rovira E. Laukhina 2007 Amabilino DB Supramolecular conducting nanowires from organogels. Angew Chem Int Ed 46 238 241
32. J. Puigmartí-Luis E.E. Laukhina V.N. Laukhin P. del Pino N. Mestres J. Vidal-Gancedo C. Rovira D.B. Amabilino 2009 Rich phase behavior in a supramolecular conducting material derived from an organogelator Adv Funct Mater 19 934 941 10.1002/adfm.200801082
33. J. Puigmartí-Luis P. del Pino E. Laukhina J. Esquena V. Laukhin C. Rovira J. Vidal-Gancedo A.G. Kanaras R.J. Nichols M. Brust D.B. Amabilino 2008 Shaping supramolecular nanofibers with nanoparticles forming complementary hydrogen bonds Angew Chem Int Ed 47 1861 1865 10.1002/anie.200704864
34. I. Danila F. Riobé J. Puigmartí-Luis P. del Pino J.D. Wallis D.B. Amabilino N. Avarvari 2009 Supramolecular electroactive organogel and conducting nanofibers with C3-symmetrical architectures J Mater Chem 19 4495 4504 10.1039/b822884a 1:CAS:528:DC%2BD1MXnslyls74%3D
35. J. Puigmartí-Luis P. del Pino V. Laukhin L.N. Feldborg C. Rovira E. Laukhina D.B. Amabilino 2010 Solvent effect on the morphology and function of novel gel-derived molecular materials J Mater Chem 20 466 474 10.1039/b917751e
36. T. Akutagawa K. Kakiuchi T. Hasegawa S.I. Noro T. Nakamura H. Hasegawa S. Mashiko J. Becher 2005 Molecularly assembled nanostructures of a redox-active organogelator Angew Chem Int Ed 44 7283 7287 10.1002/anie.200502336 1:CAS:528:DC%2BD2MXht1Kqtr3K (Pubitemid 41641751)
37. Yang Z, Liang G, Xu B. Supramolecular hydrogels based on β-amino acid derivatives. Chem Commun, 2006, 738-740 (Pubitemid 43247105)
38. Z. Yang G. Liang L. Wang B. Xu 2006 Using a kinase/phosphatase switch to regulate a supramolecular hydrogel and forming the supramolecular hydrogel in vivo J Am Chem Soc 128 3038 3043 10.1021/ja057412y 1:CAS:528: DC%2BD28Xht1Cjs70%3D
39. Yang Z, Gu H, Zhang Y, Wang L, Xu B. Small molecule hydrogels based on a class of antiinflammatory agents. Chem Commun, 2004, 208-209 (Pubitemid 38130550)
40. B. Xing C.W. Yu K.H. Chow P.L. Ho D. Fu B. Xu 2002 Hydrophobic interaction and hydrogen bonding cooperatively confer a vancomycin hydrogel: A potential candidate for biomaterials J Am Chem Soc 124 14846 14847 10.1021/ja028539f 1:CAS:528:DC%2BD38XovVCht7w%3D (Pubitemid 36014083)