Synthesis, spectroscopic, and electrochemical properties of two dyads consisted of tetrathiafulvalene and carbazole

doi:10.1007/s11705-009-0015-x

Front Chem Eng Chin

2009, Vol. 3

Issue (2) : 192-195 https://doi.org/10.1007/s11705-009-0015-x

RESEARCH ARTICLE

Synthesis, spectroscopic, and electrochemical properties of two dyads consisted of tetrathiafulvalene and carbazole

Guoqiao LAI¹, Yibo LIU², Meijiang LI¹, Yongjia SHEN²(

)

1. Key Lab of Organosilicon Chemistry and Material Technology of Ministry of Education, Hangzhou Normal University, Hangzhou 310012, China; 2. Laboratory for Advanced Materials and Institute of Fine Chemicals, East China University of Science & Technology, Shanghai 200237, China

Download: PDF(105 KB) HTML
Export: BibTeX | EndNote | Reference Manager | ProCite | RefWorks

Abstract

Two donor-σ-acceptor molecules containing tetrathiafulvalene (TTF) and carbazole moieties were synthesized by the reaction of 9-(4-bromo-butyl)-carbazole (1) with 2,6-bis(hexylthio)-3-(2-cyanoethylthio)-7-(methylthio)-tetrathiafulvalene (2) or 2,6-bis(2-cyanoethylthio)-3,7-bis(methylthio)tetrathiafulvalene (3) in the presence of CsOH·H₂O, respectively. The structures of the molecules were characterized by ¹H NMR, ¹³C NMR, MS, and elemental analyses. They showed negligible intramolecular charge-transfer interaction in their ground states as indicated by their UV-Vis spectroscopics and cyclic voltammetry results. Compared with carbazole, their fluorescence was strongly quenched, which implied that a photo induced electron transfer (PET) interaction between TTF and carbazole moieties occurred.

Keywords donor-σ-acceptor molecule intramolecular charge transfer interaction photo induced electron transfer tetrathiafulvalene carbazole

Corresponding Author(s): SHEN Yongjia,Email:yjshen@ecust.edu.cn

Issue Date: 05 June 2009

Cite this article:

Guoqiao LAI,Yibo LIU,Meijiang LI, et al. Synthesis, spectroscopic, and electrochemical properties of two dyads consisted of tetrathiafulvalene and carbazole[J]. Front Chem Eng Chin, 2009, 3(2): 192-195.

URL:

https://academic.hep.com.cn/fcse/EN/10.1007/s11705-009-0015-x
https://academic.hep.com.cn/fcse/EN/Y2009/V3/I2/192

Fig.1 Structures of compounds -

Fig.2 Synthetic route of compounds and

Tab.1 Electrochemical data of compounds , , , and

Fig.3 Fig. 2 UV-Vis absorption spectra of compound , , and in dichloromethane (10 mol/L)

Fig.4 Fluorescence emission spectra of compound , , and in dichloromethane (10 mol/L), excited at 320 nm

1	Aviram A, Ratner M. Molecular rectifiers. Chem Phys Lett , 1974, 29: 277-286 doi: 10.1016/0009-2614(74)85031-1
2	Khodorkovsky V, Becker J Y. In Organic Conductors: Fundamentals and Applications. New York: Matcel Dekker, 1994, 75-88
3	Marder S R, Kippelen B, Jen A K Y, Peyghambarian N. Design and synthesis of chromophores and polymers for electro-optic and photorefractive applications. Nature , 1997, 388: 845-851 doi: 10.1038/42190
4	Imahori H, Sakata Y. Donor-linked fullerenes: photoinduced electron transfer and its potential application. Adv Mater , 1997, 9: 537-546 doi: 10.1002/adma.19970090704
5	Bryce M R. Tetrathiafulvalenes as π-electron donors for intramolecular charge-transfer materials. Adv Mater , 1999, 11: 11-23 doi: 10.1002/(SICI)1521-4095(199901)11:1<11::AID-ADMA11>3.0.CO;2-3
6	Tsiperman E, Regev L, Becher J Y, Bernstein J, Ellern A, Khodorkovsky V, Shames A, Shapiro L. Synthesis of a novel rigid tetrathiafulvalene-s-p-benzoquinone diad (TTF-σ-Q) with inherent structural configuration suitable for intramolecular charge-transfer. Chem Commun , 1999, 1125-1126 doi: 10.1039/a902277e
7	Nielsen M B, Hansen J G, Becher J. Self-complexing tetrathiafulvalene-based donor-acceptor macrocycles. Eur J Org Chem , 1999, 2807-2815
8	Sadaike S I, Takimiya K, Aso Y, Otsubo T. TTF-porphyrin dyads as novel photoinduced electron transfer systems. Tetrahedron Lett , 2003, 44: 161-165 doi: 10.1016/S0040-4039(02)02474-7
9	Martín N, Sánchez L, Herranz M A, Guldi D M. Evidence for two separate one-electron transfer events in excited fulleropyrrolidine dyads containing tetrathiafulvalene (TTF). J Phys Chem A , 2000, 104: 4648-4657 doi: 10.1021/jp9941458
10	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 doi: 10.1021/jo961782a
11	Li S F, Zhong G Y, Zhu W H, Li F Y, Pan J F, Huang W, Tian H. Dendritic europium complex as single dopant for white-light electroluminescent device. J Mater Chem , 2005, 15: 3221-3228 doi: 10.1039/b504738b
12	Tabei E, Fukushima M, Mori S. Conductivity of doped N-carbazolyl-substituted polysilanes. Synth Met , 1995, 73: 113-116 doi: 10.1016/0379-6779(95)03321-1
13	Chun H, Moon I K, Shin D H, Kim N. Preparation of highly efficient polymeric photorefractive composite containing an isophorone-based NLO chromophore. Chem Mater , 2001, 13: 2813-2817 doi: 10.1021/cm000913s
14	Lee J H, Park J W, Choia S K. Synthesis and electroluminescent property of a new conjugated polymer based on carbazole derivative: poly(3,6-N-2-ethylhexyl carbazolyl cyanoterephthalidene). Synth Met , 1997, 88: 31-35 doi: 10.1016/S0379-6779(97)80880-6
15	Simonsen K B, Svenstrup N, Lau J, Simonsen O, MΦrk P, Kristensen G J, Becher J. Sequential functionalisation of bis-protected tetrathiafulvalene-dithiolates. Synthesis , 1996, 3: 407-418 doi: 10.1055/s-1996-4216
16	Miguel P, Bryce M R, Goldenberg L M, Beeby A, Khodorkovsky V, Shapiro L, Niemz A, Cuello A O, Rotello V. Synthesis and intramolecular charge-transfer properties of new tetrathiafulvalene-tetracyanoanthraquinodimethane diad (TTF–σ-TCNAQ) and triad (TTF–σ-TCNAQ–σ-TTF) molecules. J Mater Chem , 1998, 8: 71-76 doi: 10.1039/a704013j
17	Bang K S, Nielsen M B, Zubarev R, Becher J. Tetrathiafulvalene-phenanthroline macrocycles as redox responsive sensors for metal ions. Chem Commun , 2000, 215-216 doi: 10.1039/a909320f
18	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 doi: 10.1021/ol036511i
19	Flood A H, Nygaard S, Laursen B W, Jeppesen J O, Stoddart J. Locking down the electronic structure of (monopyrrolo)tetrathiafulvalene in [2] rotaxanes. Org Lett , 2006, 8: 2205-2208 doi: 10.1021/ol060319+

[1]	Meijiang LI, Rui HUANG, Changzhi WU, Hujin ZUO, Guoqiao LAI, Yongjia SHEN. Synthesis and properties of tetrathiafulvalene-porphyrin assemblies[J]. Front Chem Sci Eng, 2011, 5(4): 422-428.
[2]	SUN Guida, LI Cuiqing, ZHOU Zhijun, LI Fengyan. Synthesis, characterization and hydrotreating performance of supported tungsten phosphide catalysts[J]. Front. Chem. Sci. Eng., 2008, 2(2): 155-164.

Viewed

Full text

Abstract

Cited

Shared

Discussed