, -methoxyphenyl)-4'-(ethynyl)aniline (232 mg, 0.704 mmol), 4-iodopyridine (159 mg, 0.776 mmol) and CuI (3 mg, 0.016 mmol) were dissolved in anhydrous dioxane/trimethylamine 4:1 (25 mL) and argon was bubbled through for 5 min, followed by the addition of Pd(PPh 3 ) 4 (16 mg, 0.014 mmol). The resulting mixture was stirred at 90 °C for 18 h. After cooling, the solvents were removed under vacuum. The residue was diluted with CH 2 Cl 2 (50 mL) and saturated aqueous NH 4 Cl (70 mL). The aqueous layer was washed with CH 2 Cl 2 (2 × 30 mL). The combined organic layers were washed with brine (50 mL) and dried, a Schlenk tube under an inert atmosphere of argon, N,N-bis

H. Nmr, 500 MHz, CDCl 3 ): ? = 3.79 (s, 6H), 6.82-6.86 (m, 6H), 7.06-7.08 (m, 4H), 7.30-7.32 (m, 4H), 8.53-8.55 (m, 2H) ppm. 13 C NMR (125 MHz

, HRMS (MALDI) m/z calcd. for C 27 H 22 N 2 O 2 : 406.1676, vol.36

N. and N. , Purification by column chromatography afforded the pure chromophore 4 as a yellow solid (112 mg, 0.171 mmol, 56%). 1 H NMR (500 MHz, CDCl 3 ): ? = 7.30-7.33 (m, 4H), 7.39-7.41 (m, 2H), 7.44-7.47 (m, 8H), 7.50-7.56 (m, 10H), 7.66-7.68 (m, 2H), 8.16-8.18 (m, 4H)

H. N. Kim, Z. Guo, W. Zhu, J. Yoon, and H. Tian, Chem. Soc. Rev, vol.40, pp.366-375, 2011.

Y. Ohmori, Laser Photonics Rev, vol.4, pp.300-310, 2009.

A. Mishra, P. Bäuerle-;-c.-duan, and F. , Angew. Chem. Int. Ed, vol.51, 2012.

Y. Huang and . Cao, J. Mater. Chem. C, vol.22, pp.10416-10434, 2012.

. Nguyen, Chem. Mater, vol.23, pp.471-782, 2011.

J. Liang, ). Y. Chen-;-b, W. Wu, and . Zhu, Chem. Soc. Rev, vol.42, pp.3453-4388, 2013.

). J. Clifford, E. Martinez-ferrero, A. Viterisi, and E. Palomares, Chem. Soc. Rev, vol.40, pp.1635-1646, 2011.

A. Facchetti, . Mater, ). H. Today-;-b, and . Sirringhaus, Opto-Electron. Rev, vol.10, pp.121-136, 2007.

M. Pawlicki, H. A. Collins, R. G. Denning, H. L. Anderson-;-b)-g, L. He et al., Angew. Chem. Int. Ed, vol.48, pp.74-84, 2008.

F. Bure? and . Adv, , vol.4, pp.58826-58851, 2014.

C. Moreno-yruela, J. Garín, S. Orduna, E. Quintero, J. T. Navarrete et al.,

B. Diosdado, J. Villacampa, R. Casado, and . Andreu, J. Org. Chem, vol.80, pp.12115-12128, 2015.

, Accepted Manuscript

P. Solanke, S. Achelle, N. Cabon, O. Pytela, A. Barsella et al., Dyes Pigm, vol.134, pp.129-138, 2016.

R. Wu, L. Yin, Y. Li, S. C. Mater-;-b, ). K. Hoffert et al., Eur. J. Org. Chem, vol.59, pp.4230-4240, 2013.

M. Klikar, P. Solanke, J. Tydlitát, and F. Bure?, Chem. Rec, vol.16, pp.1886-1905, 2016.

S. Katan, M. H. Tretiak, A. J. Werts, R. J. Bain, N. Marsh et al., J. Phys. Chem. B, vol.111, pp.9468-9483, 2007.

N. Sun, S. Meng, D. Chao, Z. Zhou, Y. Du et al., ACS Appl. Mater. Interfaces, vol.7, pp.39218-39227, 2015.

S. Achelle, S. Kahlal, A. Barsella, J. Saillard, X. Che et al., Dyes Pigm, vol.113, pp.562-570, 2015.

A. Pytela, K. D. Barsella, F. Dorkenno, F. Robin-le-guen, S. Bure? et al., , vol.82, pp.9435-9451, 2017.

K. Olesiak-banska, M. Matczyszyn, M. G. Samoc, M. Humphrey, F. Blanchard-desce et al., Chem. Eur. J, vol.22, pp.10155-10167, 2016.

W. Shi, T. Kinoshita, and D. K. Ng, Asian J. Org. Chem, vol.6, pp.1476-1485, 2017.

Y. Ferdowsi, W. Saygili, T. Zhang, L. Edvinson, J. Kavan et al.,

A. Gratzel and . Hagfeldt, ChemSusChem, vol.11, pp.494-502, 2018.

T. Wong, C. Huang, S. Wu, F. Chou, S. Lin et al., J. Mater. Chem, vol.21, pp.5950-5958, 2011.

O. Kwon, S. Barlow, S. A. Odom, L. Beverina, N. J. Thompson et al., J. Phys. Chem. A, vol.109, pp.9346-9352, 2005.

I. Malina, V. Kampars, B. Turovska, S. Belyakov, and D. Pigm, , vol.139, pp.820-830, 2017.

H. Agnihotri, P. Mahalingevelar, H. Mande, P. Ghalsasi, and S. Kanvah, Dyes Pigm, vol.123, pp.341-348, 2015.

C. Katan, S. Tretiak, M. H. Werts, A. J. Bain, R. J. Marsh et al.,

E. Nicolaou, O. Badaeva, M. Mongin, E. Blanchard-desce-;-b)-d.-cvejn, K. Michail et al., J. Phys. Chem. B, vol.111, pp.9468-9483, 2007.

V. Ludwig, M. Giannetas, F. Fakis, . Bure?, ;. M. Adv et al., , vol.6, pp.465-474, 2016.

J. Weng, Q. Mei, Q. Fan, Q. Ling, B. Tong et al., , vol.3, pp.21877-21887, 2013.

U. Nair, Chem. Commun, vol.50, pp.6902-6905, 2014.

Z. He, C. Kan, C. Ho, W. Wong, C. Chui et al., Adv. Synth. Catal, vol.88, pp.2259-2268, 2011.

I. Bundulis, D. Mihailovs, M. Volyniuk, J. V. Rutkis, and . Grazulevicius, , vol.140, pp.431-440, 2017.

M. W. Thesen, B. Höfer, M. Debeaux, S. Janietz, A. Wedel et al., J. Polym. Sci. A Polym. Chem, vol.48, pp.5290-5293, 2010.

G. Shan, H. Li, J. Qin, D. Zhu, Y. Liao et al., , vol.41, pp.9590-593, 2012.

). Y. Chem, Y. Jin, and . Qian, New J. Chem, vol.2, pp.2872-2880, 2014.

D. S. Kopchuk, A. P. Krinochin, E. S. Starnovskaya, Y. K. Shtaitz, A. F. Khasanov et al.,

S. Taniya, S. Santra, G. V. Zyryanov, A. Majee, V. L. Rusinov et al., Chem. Select, vol.3, pp.4141-4146, 2018.

R. Pasini, M. Adv-;-c)-y.-qian, ). E. Luo-;-d, C. Cariati, E. Dragonetti et al., Chem. Commun, vol.5, pp.1608-1610, 2014.

Y. Shao, J. Zhong, and . Yao, Sci. China Chem, vol.61, pp.545-556, 2018.

J. Ma, W. Li, J. Li, R. Shi, G. Yin et al., Talanta, vol.182, pp.464-469, 2018.

P. Kachwal, H. R. Alarn, S. S. Yadav, A. R. Pasha, I. R. Choudhury et al., New J. Chem, vol.42, pp.1133-1140, 2018.

J. Tydlitát, S. Achelle, J. Rodríguez-lópez, O. Pytela, T. Mikýsek et al., , vol.145, pp.467-478, 2017.

C. Allain, F. Schmidt, R. Lartia, G. Bordeau, C. Fiorini-debuiscschert et al., ChemBioChem, vol.8, pp.424-433, 2007.

S. Kato, Y. Yamada, H. Hiyoshi, K. Umezu, and Y. Nakamura, J. Org. Chem, vol.80, pp.9076-9090, 2015.

D. F. Eaton, Pure Appl. Chem, vol.60, pp.1107-1114, 1988.

R. Lartia, C. Allain, G. Bordeau, F. Schmidt, C. Fiorini-debuisschert et al.,

J. Teulade-fichou, . Org, S. Chem-;-b)-f.-mahuteau-betzer, and . Piguel, J. Photochem. Photobiol. A, vol.73, pp.281-286, 2008.

C. Reichardt, Chem. Rev, vol.94, pp.2319-2358, 1994.

D. Bao, B. Millare, W. Xia, B. G. Steyer, A. A. Gerasimenko et al.,

, Vullev J. Phys. Chem. A, vol.113, pp.1259-1267, 2009.

M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb et al.,

B. G. Bloino, R. Janesko, B. Gomperts, H. P. Mennucci, J. V. Hratchian et al.,

J. L. Izmaylov, D. Sonnenberg, F. Williams-young, F. Ding, F. Lipparini et al.,

A. Peng, T. Petrone, D. Henderson, V. G. Ranasinghe, J. Zakrzewski et al.,

W. Zheng, M. Liang, M. Hada, K. Ehara, R. Toyota et al.,

Y. Nakajima, O. Honda, H. Kitao, T. Nakai, K. Vreven et al.,

E. Peralta, F. Ogliaro, M. J. Bearpark, J. J. Heyd, E. N. Brothers et al.,

T. A. Staroverov, R. Keith, J. Kobayashi, K. Normand, A. P. Raghavachari et al.,

S. S. Burant, J. Iyengar, M. Tomasi, J. M. Cossi, M. Millam et al.,

W. Ochterski, R. L. Martin, K. Morokuma, O. Farkas, J. B. Foresman et al., , 2016.

A. C. Spivey, L. Shukla, and J. D. Hayler, Org. Lett, vol.9, pp.891-894, 2007.

O. Opchem and . Pytela,

C. Lambert, G. Nöll, E. Schmälzlin, K. Meerholz, and C. Bräuchle, Chem. Eur. J, vol.4, pp.2129-2135, 1998.

S. Mathew and H. Imahori, J. Mater. Chem, vol.21, pp.7166-7174, 2011.

Y. Hua, B. Xu, P. Liu, H. Chen, H. Tian et al., Chem. Sci, vol.7, pp.2633-2638, 2016.

C. Lambert, W. Gaschler, G. Nöll, M. Weber, E. Schmälzlin et al., J. Chem. Soc, pp.964-974, 2001.