17 Azulene-Based Materials for Organic Field-Effect Transistors
357
7. Smits, E.C.P., Setayesh, S., Anthopoulos, T.D., Buechel, M., Nijssen, W., Coehoorn, R., Blom,
P.W.M., de Boer, B., de Leeuw, D.M.: Near-infrared light-emitting ambipolar organic fieldeffect transistors. Adv. Mater. 19, 734–738 (2007)
8. Wöbkenberg, P.H., Labram, J.G., Swiecicki, J.-M., Parkhomenko, K., Sredojevic, D., Gisselbrecht, J.-P., de Leeuw, D.M., Bradley, D.D.C., Djukic, J.-P., Anthopoulos, T.D.: Ambipolar
organic transistors and near-infrared phototransistors based on a solution-processable squarilium dye. J. Mater. Chem. 20, 3673–3680 (2010)
9. Michl, J., Thulstrup, E.W.: Why is azulene blue and anthracene white? A simple mo picture.
Tetrahedron 32, 205–209 (1976)
10. Lemal, D.M., Goldman, G.D.: Synthesis of azulene, a blue hydrocarbon. J. Chem. Educ. 65,
923–933 (1988)
11. Murai, M., Amir, E., Amir, R.J., Hawker, C.J.: Azulene-based conjugated polymers: unique
seven-membered ring connectivity leading to stimuli-responsiveness. Chem. Sci. 3, 2721–2725
(2012)
12. Amir, E., Murai, M., Amir, R.J., Chabinyc, M.L., Chabinyc, M.L., Hawker, C.J.: Conjugated oligomers incorporating azulene building blocks—seven—versus five-membered ring
connectivity. Chem. Sci. 5, 4483–4489 (2014)
13. Shevyakov, S.V., Li, H., Muthyala, R., Asato, A.E., Croney, J.C., Jameson, D.M., Liu, R.S.H.:
Orbital control of the color and excited state properties of formylated and fluorinated derivatives
of azulene†. J. Phys. Chem. A 107, 3295–3299 (2003)
14. Shoji, T., Maruyama, A., Araki, T., Ito, S., Okujima, T.: Synthesis of 2- and 6-thienylazulenes
by palladium-catalyzed direct arylation of 2- and 6-haloazulenes with thiophene derivatives.
Org. Biomol. Chem. 13, 10191–10197 (2015)
15. Anthony, J.E.: Functionalized acenes and heteroacenes for organic electronics. Chem. Rev.
106, 5028–5048 (2006)
16. Mei, J., Diao, Y., Appleton, A.L., Fang, L., Bao, Z.: Integrated materials design of organic
semiconductors for field-effect transistors. J. Am. Chem. Soc. 135, 6724–6746 (2013)
17. Dong, H., Fu, X., Liu, J., Wang, Z., Hu, W.: 25th anniversary article: key points for high-mobility
organic field-effect transistors. Adv. Mater. 25, 6158–6183 (2013)
18. Gavezzotti, A., Desiraju, G.R.: A systematic analysis of packing energies and other packing
parameters for fused-ring aromatic hydrocarbons. Acta Crystallogr., Sect. B: Struct. Sci. 44,
427–434 (1988)
19. Desiraju, G.R., Gavezzotti, A.: Crystal structures of polynuclear aromatic hydrocarbons. Classification, rationalization and prediction from molecular structure. Acta Crystallogr., Sect. B:
Struct. Sci. 45, 473–482 (1989)
20. Nozoe, T., Seto, S., Matsumura, S., Asano, T.: Synthesis of azulene derivatives from troponoids
and cyanoacetic ester. Proc. Japan Acad. 32, 339–343 (1956)
21. Nozoe, T., Seto, S., Matsumura, S.: Synthesis of 2-substituted azulenes by nucleophilic
substitution reactions of 2-haloazulene derivatives. Bull. Chem. Soc. Jpn 35, 1990–1998 (1962)
22. Tian, H.K., Shi, J.W., He, B., Hu, N.H., Dong, S.Q., Yan, D.H., Zhang, J.P., Geng, Y.H., Wang,
F.S.: Naphthyl and thionaphthyl end-capped oligothiophenes as organic semiconductors: effect
of chain length and end-capping groups. Adv. Funct. Mater. 17, 1940–1951 (2007)
23. Nicolas, Y., Blanchard, P., Roncali, J., Allain, M., Mercier, N., Deman, A.-L., Tardy, J.:
Synthesis of a thermally stable hybrid acene-thiophene organic semiconductor via a soluble
precursor. Org. Lett. 7, 3513–3516 (2005)
24. Yamaguchi, Y., Maruya, Y., Katagiri, H., Nakayama, K.-I., Ohba, Y.: Synthesis, properties,
and OFET characteristics of 5,5 -Di(2-azulenyl)-2,2 -bithiophene (DAzBT) and 2,5-Di(2azulenyl)-thieno[3,2- b]thiophene (DAzTT). Org. Lett. 14, 2316–2319 (2012)
25. Yamaguchi, Y., Ogawa, K., Nakayama, K.-I., Ohba, Y., Katagiri, H.: Terazulene: a highperformance n-type organic field-effect transistor based on molecular orbital distribution
control. J. Am. Chem. Soc. 135, 19095–19098 (2013)
26. Yamaguchi, Y., Takubo, M., Ogawa, K., Nakayama, K.-I., Koganezawa, T., Katagiri, H.: Terazulene isomers: polarity change of OFETs through molecular orbital distribution contrast. J. Am.
Chem. Soc. 138, 11335–11343 (2016)
357
7. Smits, E.C.P., Setayesh, S., Anthopoulos, T.D., Buechel, M., Nijssen, W., Coehoorn, R., Blom,
P.W.M., de Boer, B., de Leeuw, D.M.: Near-infrared light-emitting ambipolar organic fieldeffect transistors. Adv. Mater. 19, 734–738 (2007)
8. Wöbkenberg, P.H., Labram, J.G., Swiecicki, J.-M., Parkhomenko, K., Sredojevic, D., Gisselbrecht, J.-P., de Leeuw, D.M., Bradley, D.D.C., Djukic, J.-P., Anthopoulos, T.D.: Ambipolar
organic transistors and near-infrared phototransistors based on a solution-processable squarilium dye. J. Mater. Chem. 20, 3673–3680 (2010)
9. Michl, J., Thulstrup, E.W.: Why is azulene blue and anthracene white? A simple mo picture.
Tetrahedron 32, 205–209 (1976)
10. Lemal, D.M., Goldman, G.D.: Synthesis of azulene, a blue hydrocarbon. J. Chem. Educ. 65,
923–933 (1988)
11. Murai, M., Amir, E., Amir, R.J., Hawker, C.J.: Azulene-based conjugated polymers: unique
seven-membered ring connectivity leading to stimuli-responsiveness. Chem. Sci. 3, 2721–2725
(2012)
12. Amir, E., Murai, M., Amir, R.J., Chabinyc, M.L., Chabinyc, M.L., Hawker, C.J.: Conjugated oligomers incorporating azulene building blocks—seven—versus five-membered ring
connectivity. Chem. Sci. 5, 4483–4489 (2014)
13. Shevyakov, S.V., Li, H., Muthyala, R., Asato, A.E., Croney, J.C., Jameson, D.M., Liu, R.S.H.:
Orbital control of the color and excited state properties of formylated and fluorinated derivatives
of azulene†. J. Phys. Chem. A 107, 3295–3299 (2003)
14. Shoji, T., Maruyama, A., Araki, T., Ito, S., Okujima, T.: Synthesis of 2- and 6-thienylazulenes
by palladium-catalyzed direct arylation of 2- and 6-haloazulenes with thiophene derivatives.
Org. Biomol. Chem. 13, 10191–10197 (2015)
15. Anthony, J.E.: Functionalized acenes and heteroacenes for organic electronics. Chem. Rev.
106, 5028–5048 (2006)
16. Mei, J., Diao, Y., Appleton, A.L., Fang, L., Bao, Z.: Integrated materials design of organic
semiconductors for field-effect transistors. J. Am. Chem. Soc. 135, 6724–6746 (2013)
17. Dong, H., Fu, X., Liu, J., Wang, Z., Hu, W.: 25th anniversary article: key points for high-mobility
organic field-effect transistors. Adv. Mater. 25, 6158–6183 (2013)
18. Gavezzotti, A., Desiraju, G.R.: A systematic analysis of packing energies and other packing
parameters for fused-ring aromatic hydrocarbons. Acta Crystallogr., Sect. B: Struct. Sci. 44,
427–434 (1988)
19. Desiraju, G.R., Gavezzotti, A.: Crystal structures of polynuclear aromatic hydrocarbons. Classification, rationalization and prediction from molecular structure. Acta Crystallogr., Sect. B:
Struct. Sci. 45, 473–482 (1989)
20. Nozoe, T., Seto, S., Matsumura, S., Asano, T.: Synthesis of azulene derivatives from troponoids
and cyanoacetic ester. Proc. Japan Acad. 32, 339–343 (1956)
21. Nozoe, T., Seto, S., Matsumura, S.: Synthesis of 2-substituted azulenes by nucleophilic
substitution reactions of 2-haloazulene derivatives. Bull. Chem. Soc. Jpn 35, 1990–1998 (1962)
22. Tian, H.K., Shi, J.W., He, B., Hu, N.H., Dong, S.Q., Yan, D.H., Zhang, J.P., Geng, Y.H., Wang,
F.S.: Naphthyl and thionaphthyl end-capped oligothiophenes as organic semiconductors: effect
of chain length and end-capping groups. Adv. Funct. Mater. 17, 1940–1951 (2007)
23. Nicolas, Y., Blanchard, P., Roncali, J., Allain, M., Mercier, N., Deman, A.-L., Tardy, J.:
Synthesis of a thermally stable hybrid acene-thiophene organic semiconductor via a soluble
precursor. Org. Lett. 7, 3513–3516 (2005)
24. Yamaguchi, Y., Maruya, Y., Katagiri, H., Nakayama, K.-I., Ohba, Y.: Synthesis, properties,
and OFET characteristics of 5,5 -Di(2-azulenyl)-2,2 -bithiophene (DAzBT) and 2,5-Di(2azulenyl)-thieno[3,2- b]thiophene (DAzTT). Org. Lett. 14, 2316–2319 (2012)
25. Yamaguchi, Y., Ogawa, K., Nakayama, K.-I., Ohba, Y., Katagiri, H.: Terazulene: a highperformance n-type organic field-effect transistor based on molecular orbital distribution
control. J. Am. Chem. Soc. 135, 19095–19098 (2013)
26. Yamaguchi, Y., Takubo, M., Ogawa, K., Nakayama, K.-I., Koganezawa, T., Katagiri, H.: Terazulene isomers: polarity change of OFETs through molecular orbital distribution contrast. J. Am.
Chem. Soc. 138, 11335–11343 (2016)