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Chemical Compound Review

terthienyl     2,5-dithiophen-2-ylthiophene

Synonyms: a-terthienyl, CHEMBL90017, SureCN147274, ACMC-1BU3D, AG-D-24304, ...
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Disease relevance of Terthiophene


High impact information on Terthiophene


Chemical compound and disease context of Terthiophene


Biological context of Terthiophene


Anatomical context of Terthiophene


Associations of Terthiophene with other chemical compounds


Gene context of Terthiophene

  • Hexamer 1(6T) was synthesized by oxidative coupling of terthiophene 12, tris-annelated with BCO units, in 81% yield [23].
  • The triplet energy of alpha-terthienyl has been determined by heavy atom-induced optical absorption: the value of 39.7 +/- 1.5 kcal/mol is consistent with earlier energy transfer work [24].

Analytical, diagnostic and therapeutic context of Terthiophene


  1. Characterization of cutaneous phototoxicity induced by topical alpha-terthienyl and ultraviolet A radiation. Rampone, W.M., McCullough, J.L., Weinstein, G.D., Towers, G.H., Berns, M.W., Abeysekera, B. J. Invest. Dermatol. (1986) [Pubmed]
  2. Structure-activity studies of photoactivated antiviral and cytotoxic tricyclic thiophenes. Marles, R.J., Hudson, J.B., Graham, E.A., Soucy-Breau, C., Morand, P., Compadre, R.L., Compadre, C.M., Towers, G.H., Arnason, J.T. Photochem. Photobiol. (1992) [Pubmed]
  3. Intracellular target for alpha-terthienyl photosensitization: involvement of lysosomal membrane damage. Sasaki, M., Koyama, S., Tokiwa, K., Fujita, H. Photochem. Photobiol. (1993) [Pubmed]
  4. Photoactive terthiophenes: the influence of serum on anti-HIV (human immunodeficiency virus) activities. Hudson, J.B., Marles, R.J., Soucy-Breau, C., Harris, L., Arnason, J.T. Photochem. Photobiol. (1994) [Pubmed]
  5. Photodynamic hemolysis caused by alpha-terthienyl. Yamamoto, E., MacRae, W.D., Garcia, F.J., Towers, G.H. Planta Med. (1984) [Pubmed]
  6. Photoactivation of the nematicidal compound alpha-terthienyl from roots of marigolds (Tagetes species). A possible singlet oxygen role. Bakker, J., Gommers, F.J., Nieuwenhuis, I., Wynberg, H. J. Biol. Chem. (1979) [Pubmed]
  7. Exploration of ground and excited electronic states of aromatic and quinoid S,S-dioxide terthiophenes. Complementary systems for enhanced electronic organic materials. Casado, J., Zgierski, M.Z., Ewbank, P.C., Burand, M.W., Janzen, D.E., Mann, K.R., Pappenfus, T.M., Berlin, A., Pérez-Inestrosa, E., Ortiz, R.P., López Navarrete, J.T. J. Am. Chem. Soc. (2006) [Pubmed]
  8. Thiophene dendron jacketed poly(amidoamine) dendrimers: nanoparticle synthesis and adsorption on graphite. Deng, S., Locklin, J., Patton, D., Baba, A., Advincula, R.C. J. Am. Chem. Soc. (2005) [Pubmed]
  9. Charge-transfer mechanism for cytochrome c adsorbed on nanometer thick films. Distinguishing frictional control from conformational gating. Khoshtariya, D.E., Wei, J., Liu, H., Yue, H., Waldeck, D.H. J. Am. Chem. Soc. (2003) [Pubmed]
  10. A theoretical study on the low-lying excited states of 2,2':5',2''-terthiophene and 2,2':5',2'':5'',2'''-quaterthiophene. Rubio, M., Merchán, M., Ortí, E. Chemphyschem : a European journal of chemical physics and physical chemistry. (2005) [Pubmed]
  11. The anti-HIV activities of photoactive terthiophenes. Hudson, J.B., Harris, L., Marles, R.J., Arnason, J.T. Photochem. Photobiol. (1993) [Pubmed]
  12. UV-A coexposure enhances the toxicity of aromatic hydrocarbons, munitions, and metals to Photobacterium phosphoreum. Arfsten, D.P., Davenport, R., Schaeffer, D.J. Biomed. Environ. Sci. (1994) [Pubmed]
  13. Synergistic insecticidal mode of action between sesquiterpene lactones and a phototoxin, alpha-terthienyl. Guillet, G., Harmatha, J., Waddell, T.G., Philogène, B.J., Arnason, J.T. Photochem. Photobiol. (2000) [Pubmed]
  14. Novel protein kinase C inhibitors: synthesis and PKC inhibition of beta-substituted polythiophene derivatives. Xu, W.C., Zhou, Q., Ashendel, C.L., Chang, C.T., Chang, C.J. Bioorg. Med. Chem. Lett. (1999) [Pubmed]
  15. Examination of naturally occurring polyacetylenes and alpha-terthienyl for their ability to induce cytogenetic damage. MacRae, W.D., Chan, G.F., Wat, C.K., Towers, G.H., Lam, J. Experientia (1980) [Pubmed]
  16. Pharmacokinetics, metabolism and toxicity of the plant-derived photoxin alpha-terthienyl. Marles, R., Durst, T., Kobaisy, M., Soucy-Breau, C., Abou-Zaid, M., Arnason, J.T., Kacew, S., Kanjanapothi, D., Rujjanawate, C., Meckes, M. Pharmacol. Toxicol. (1995) [Pubmed]
  17. Photoinactivation of human erythrocyte enzymes by alpha-terthienyl and phenylheptatriyne, naturally occurring compounds in the Asteraceae. Yamamoto, E., Wat, C.K., MacRae, W.D., Towers, G.H., Chan, C.F. FEBS Lett. (1979) [Pubmed]
  18. Phototoxic process after rapid photosensitive membrane damage of 5,5"-bis(aminomethyl)-2,2':5',2"-terthiophene dihydrochloride. Saito, T.K., Takahashi, M., Muguruma, H., Niki, E., Mabuchi, K. J. Photochem. Photobiol. B, Biol. (2001) [Pubmed]
  19. Tuning from pi,pi to charge-transfer excited states in styryl-substituted terthiophenes: an ultrafast and steady-state emission study. Clarke, T.M., Gordon, K.C., Kwok, W.M., Phillips, D.L., Officer, D.L. The journal of physical chemistry. A, Molecules, spectroscopy, kinetics, environment & general theory. (2006) [Pubmed]
  20. Identification of carotenoids in Erwinia herbicola and in a transformed Escherichia coli strain. Sandmann, G., Woods, W.S., Tuveson, R.W. FEMS Microbiol. Lett. (1990) [Pubmed]
  21. The mode of action of polyacetylene and thiophene photosensitizers on liposome permeability to glucose. McRae, D.G., Yamamoto, E., Towers, G.H. Biochim. Biophys. Acta (1985) [Pubmed]
  22. Spectroscopy and transport of the triplet exciton in a terthiophene end-capped poly(phenylene ethynylene). Funston, A.M., Silverman, E.E., Schanze, K.S., Miller, J.R. The journal of physical chemistry. B, Condensed matter, materials, surfaces, interfaces & biophysical. (2006) [Pubmed]
  23. Synthesis and properties of novel oligothiophenes surrounded by bicyclo[2.2.2]octene frameworks. Wakamiya, A., Yamazaki, D., Nishinaga, T., Kitagawa, T., Komatsu, K. J. Org. Chem. (2003) [Pubmed]
  24. Efficiency of the photoprocesses leading to singlet oxygen (1 delta g) generation by alpha-terthienyl: optical absorption, optoacoustic calorimetry and infrared luminescence studies. Scaiano, J.C., Redmond, R.W., Mehta, B., Arnason, J.T. Photochem. Photobiol. (1990) [Pubmed]
  25. Raman spectroscopy of short-lived terthiophene radical cations generated by photochemical and chemical oxidation. Clarke, T.M., Gordon, K.C., Chan, W.S., Phillips, D.L., Wagner, P., Officer, D.L. Chemphyschem : a European journal of chemical physics and physical chemistry. (2006) [Pubmed]
  26. Generation of superoxide anion radical by alpha-terthienyl in the anal gills of mosquito larvae Aedes aegypti: a new aspect in alpha-terthienyl phototoxicity. Nivsarkar, M., Kumar, G.P., Laloraya, M., Laloraya, M.M. Arch. Insect Biochem. Physiol. (1992) [Pubmed]
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