Synthesis and properties of tetrathiafulvalene-fluorescein dyads

Guoqiao LAI, Yibo LIU, Yu ZHANG, Jun RUAN, Meijiang LI, Yongjia SHEN

PDF(131 KB)
PDF(131 KB)
Front. Chem. Sci. Eng. ›› 2009, Vol. 3 ›› Issue (3) : 314-317. DOI: 10.1007/s11705-009-0207-4
RESEARCH ARTICLE
RESEARCH ARTICLE

Synthesis and properties of tetrathiafulvalene-fluorescein dyads

Author information +
History +

Abstract

Two donor-acceptor molecular systems consisted of tetrathiafulvalene (TTF) and fluorescein were designed and synthesized. The target compounds and their key intermediates were characterized by 1H NMR, mass spectrography, and infrared spectroscopy, respectively. The UV-vis spectra implied intramolecular interaction in their ground state. Fluorescence spectra and fluorescence lifetimes indicated the photoinduced charge transfer (PET) interaction between the TTF and fluorescein units in their excited states.

Keywords

TTF / fluorescein / charge transfer

Cite this article

Download citation ▾
Guoqiao LAI, Yibo LIU, Yu ZHANG, Jun RUAN, Meijiang LI, Yongjia SHEN. Synthesis and properties of tetrathiafulvalene-fluorescein dyads. Front Chem Eng Chin, 2009, 3(3): 314‒317 https://doi.org/10.1007/s11705-009-0207-4

References

[1]
Bryce M R. Tetrathiafulvalenes as π-electron donors for intramolecular charge-transfer materials. Adv Mater, 1999, 11: 11-23
CrossRef Google scholar
[2]
Segura J L, Martin N. New concepts in tetrathiafulvalene chemistry. Angew Chem Int Ed, 2001, 40: 1372-1409
CrossRef Google scholar
[3]
JØrgensen T, Hansen T K, Becher J. Tetrathiafulvalenes as building-blocks in suparmolecular chemistry. Chem Soc Rev, 1994, 23: 41-51
[4]
Sadaike S I, Takimiya K, Aso Y, Otsubo T. TTF-porphyrin dyads as novel photoinduced electron transfer systems. Tetrahedron Lett, 2003, 44: 161-165
CrossRef Google scholar
[5]
Hu Y Y, Lai G Q, Shen Y J, Li Y F. Synthesis, optical spectroscopy and electrochemistry of TTF-derived metallophthalocyanine complexes. Dyes Pigments, 2005, 66: 49-53
CrossRef Google scholar
[6]
Zhang G X, Zhang D Q, Guo X F, Zhu D B. A new redox-fluorescence switch based on a triad with tetrathiafulvalene and anthracene units. Org Lett, 2004, 6: 1209-1212
CrossRef Google scholar
[7]
Leroy-Lhez S, Perrin L, Baffreau J, Hudhomme P. Perylenediimide derivatives in new donor-acceptor dyads. C R Chimie, 2006, 9: 240-246
CrossRef Google scholar
[8]
Simonsen K B, Zong K, Rogers R D, Cava M P, Becher J. Stable macrocyclic and tethered donor-acceptor systems: intramolecular bipyridinium and tetrathiafulvalene assemblies. J Org Chem, 1997, 62: 679-686
CrossRef Google scholar
[9]
Allard E, Cousseau J, Orduna J, Garin J, Luo H, Arakic Y, Ito O. Photoinduced electron-transfer processes in C60-tetrathiafulvalene dyads containing a short or long flexible spacery. Phys Chem Chem Phys, 2002, 4: 5944-5951
CrossRef Google scholar
[10]
Sun X D, Li D M, Chen G D, Zhang J L. A series of new porphyrin dyads: the synthesis and photophysical properties. Dyes Pigments, 2006, 71: 118-122
CrossRef Google scholar
[11]
Miura T, Urano Y, Tanaka Y, Nagano T, Ohkubo K, Fukuzumi S. Rational design principle for modulating fluorescence properties of fluorescein-based probes by photoinduced electron transfer. J Am Chem Soc, 2003, 125: 8666-8671
CrossRef Google scholar
[12]
Svenstrup N, Becher J. The organic chemstry of 1,3-dithiole-4,5dithilate (DMIT). Synthsis, 1995: 215-235
[13]
Song A, Zhang H, Zhang M H, Shen T. Photophysical properties of polyads containing a pluorecein moiety. Dyes Pigments, 1999, 42: 149-158
CrossRef Google scholar
[14]
Farren C, Christensen C A, Fitzgerald S, Bryce M R, Beeby A. Synthesis of novel Phthalocyanine-Tetrathiafulvalene hybrids: intramolecular fluorescence quenching related to molecular geometry. J Org Chem, 2002, 67: 9130-9139
CrossRef Google scholar
[15]
Miguel P D, Martin R B, Goldenberg L M, Beeby A, Khodorkovsky V, Shapiro L, Niemz A, Cuello A, Rotello V. Synthesis and intramolecular charge-transfer properties of new tetrathiafulvalene-σ-tetravanoanthraquinodimethane diad (TTF-σ-TCNAQ) and triad (TTF-σ-TCNAQ-σ-TTF) molecules. J Mater Chem, 1998, 8: 71-76
CrossRef Google scholar
[16]
Spanggaard H, Prehn J, Nielsen M B, Levillain E, Allain M, Becher J. Multiple-bridged bis-tetrathiafulvalenes: new synthetic protocols and spectroelectrochemical investigations. J Am Chem Soc, 2000, 122: 9486-9494
CrossRef Google scholar

Acknowledgements

This work was supported by the National Natural Science Foundation of China (Grant No. 20676036) and the Key Project of the Ministry of Education of China (No. 03053).

RIGHTS & PERMISSIONS

2014 Higher Education Press and Springer-Verlag Berlin Heidelberg
AI Summary AI Mindmap
PDF(131 KB)

Accesses

Citations

Detail

Sections
Recommended

/