One-dimensional molecular co-crystal alloys capable of full-color emission for low-loss optical waveguide and optical logic gate

Abstract

The luminescence color of molecule-based photoactive materials is the key to the applications in lighting and optical communication. Realizing continuous regulation of emission color in molecular systems is highly desirable but still remains a challenge due to the individual emission band of purely organic molecules. Herein, a novel alloy strategy based on molecular co-crystals is reported. By adjusting the molar ratio of pyrene (Py) and fluorathene (Flu), three types of molecular co-crystal alloys (MCAs) assemblies are prepared involving Py-Flu-OFN-x%, Py-Flu-TFP-x%, Py-Flu-TCNB-x%. Multiple energy level structure and Förster resonance energy transfer (FRET) process endow materials with tunable full-spectra emission color in visible region. Impressively, these MCAs and co-crystals can be successfully applied to low optical loss waveguide and optical logic gate by virtue of all-color luminescence from blue across green to red, together with smooth surface of onedimensional microrods, which show promising applications as continuous light emitters for advance photonics applications.

Keywords

full-color emission / microrods / molecular co-crystal / optical waveguide / organic alloys

References

[1] J. Feldmann, N. Youngblood, M. Karpov, H. Gehring, X. Li, M. Stappers, M. Le Gallo, X. Fu, A. Lukashchuk, A. S. Raja, J. Liu, C. D. Wright, A. Sebastian, T. J. Kippenberg, W. H. P. Pernice, H. Bhaskaran, Nature 2021, 589, 52.

[2] D. P. Karothu, G. Dushaq, E. Ahmed, L. Catalano, S. Polavaram, R. Ferreira, L. Li, S. Mohamed, M. Rasras, P. Naumov, Nat. Commun. 2021, 12, 1326.

[3] B. Zhou, Z. Qi, D. Yan, Angew. Chem. Int. Ed. 2022, 61, e202208735.

[4] C. Ríos, M. Stegmaier, P. Hosseini, D. Wang, T. Scherer, C. D. Wright, H. Bhaskaran, W. H. P. Pernice, Nat. Photonics 2015, 9, 725.

[5] J. Ravi, M. Annadhasan, A. V. Kumar, R. Chandrasekar, Adv. Funct. Mater. 2021, 31, 2100642.

[6] X. Lou, Y. Yang, J. Am. Chem. Soc. 2021, 143, 11976.

[7] F. Balzer, V. G. Bordo, A. C. Simonsen, H. G. Rubahn, Appl. Phys. Lett. 2002, 82, 10.

[8] M. Annadhasan, A. R. Agrawal, S. Bhunia, V. V. Pradeep, S. S. Zade, C. M. Reddy, R. Chandrasekar, Angew. Chem. Int. Ed. 2020, 59, 13852.

[9] R. Chandrasekar, Adv. Opt. Mater. 2023, 11, 2301124.

[10] R. Chandrasekar, Chem. Commun. 2022, 58, 3415.

[11] R. Chandrasekar, Small 2021, 17, 2100277.

[12] B. Zhou, D. Yan, Chem. Sci. 2022, 13, 7429.

[13] H. Lin, Y. Ma, S. Chen, X. Wang, Angew. Chem. Int. Ed. 2023, 62, e202214214.

[14] Z.-Q. Li, D.-X. Ma, F.-F. Xu, T.-X. Dan, Z.-L. Gong, J.-Y. Shao, Y. S. Zhao, J. Yao, Y.-W. Zhong, Angew. Chem. Int. Ed. 2022, 61, e202205033.

[15] J. M. Halabi, E. Ahmed, L. Catalano, D. P. Karothu, R. Rezgui, P. Naumov, J. Am. Chem. Soc. 2019, 141, 14966.

[16] X.-T. Liu, K. Wang, Z. Chang, Y.-H. Zhang, J. Xu, Y. S. Zhao, X.-H. Bu, Angew. Chem. Int. Ed. 2019, 58, 13890.

[17] S. Li, B. Lu, X. Fang, D. Yan, Angew. Chem. Int. Ed. 2020, 59, 22623.

[18] Y. Shi, Q. Lv, Y. Tao, Y. Ma, X. Wang, Angew. Chem. Int. Ed. 2022, 61, e202208768.

[19] M. Zhuo, Y. Tao, X. Wang, Y. Wu, S. Chen, L. Liao, L. Jiang, Angew. Chem. Int. Ed. 2018, 57, 11300.

[20] D. B. Amabilino, D. K. Smith, J. W. Steed, Chem. Soc. Rev. 2017, 46, 2404.

[21] D. Bučar, R. W. Lancaster, J. Bernstein, Angew. Chem. Int. Ed. 2015, 54, 6972.

[22] K. Liu, Y. Lei, H. Fu, Chem. Mat. 2020, 32, 5162.

[23] K. Liu, S. Li, L. Fu, Y. Lei, Q. Liao, H. Fu, Nanoscale 2022, 14, 6305.

[24] S. Ma, H. Sun, J. Chen, Y. Yu, H. Lu, S. Wang, J. Zhang, J. Zhao, G. Long, X. Wang, Adv. Opt. Mater. 2023, 11, 2203087.

[25] Y. Sun, Y. Lei, W. Hu, W. Wong, J. Am. Chem. Soc. 2020, 142, 7265

[26] J. Wang, A. Li, S. Xu, B. Li, C. Song, Y. Geng, N. Chu, J. He, W. Xu, J. Mater. Chem. C 2018, 6, 8958

[27] Y. Zhang, H. Wu, Y. Wang, L. Sun, S. Li, Y. Ren, Y. Sun, F. Yang, X. Zhang, W. Hu, J. Mater. Chem. C 2022, 10, 2562

[28] H. Ye, G. Liu, S. Liu, D. Casanova, X. Ye, X. Tao, Q. Zhang, Q. Xiong, Angew. Chem. Int. Ed. 2018, 57, 1928.

[29] Y. Huang, J. Xing, Q. Gong, L. Chen, G. Liu, C. Yao, Z. Wang, H. Zhang, Z. Chen, Q. Zhang, Nat. Commun. 2019, 10, 169.

[30] J. Jin, G. Long, Y. Gao, J. Zhang, C. Ou, C. Zhu, H. Xu, J. Zhao, M. Zhang, W. Huang, ACS Appl. Mater. Inter. 2019, 11, 1109.

[31] B. Wu, M. Zhuo, S. Chen, Y. Su, Y. Yu, J. Fan, Z. Wang, X. Wang, Adv. Opt. Mater. 11, 2023, 2202895.

[32] a) Y. Ma, H. Yin, J. Yang, H. Lin, S. Chen, J. Zhou, S. Zhuo, X. Wang, Adv. Opt. Mater. 2023, 11, 2201000. b) G. Jiang, J. Yu, J. Wang, B. Z. Tang, Aggregate 2022, 3, e285.

[33] X. Huang, X. Liu, K. Ding, S. R. Forrest, Mater. Horizons 2020, 7, 244.

[34] R. Natarajan, G. Magro, L. N. Bridgland, A. Sirikulkajorn, S. Narayanan, L. E. Ryan, M. F. Haddow, A. G. Orpen, J. P. H. Charmant, A. J. Hudson, A. P. Davis, Angew. Chem. Int. Ed. 2011, 50, 11386.

[35] K. Sada, K. Inoue, T. Tanaka, A. Epergyes, A. Tanaka, N. Tohnai, A. Matsumoto, M. Miyata, Angew. Chem. Int. Ed. 2005, 44, 7059.

[36] M. Schwarze, W. Tress, B. Beyer, F. Gao, R. Scholz, C. Poelking, K. Ortstein, A. A. Günther, D. Kasemann, D. Andrienko, K. Leo, Science 2016, 352, 1446.

[37] J. Dou, Z. Yu, J. Zhang, Y. Zheng, Z. Yao, Z. Tu, X. Wang, S. Huang, C. Liu, J. Sun, Y. Yi, X. Cao, Y. Gao, J. Wang, J. Pei, J. Am. Chem. Soc. 2019, 141, 6561.

[38] J. Zhang, W. Liu, G. Zhou, Y. Yi, S. Xu, F. Liu, H. Zhu, X. Zhu, Adv. Energy Mater. 2020, 10, 1903298.

[39] Z. Bi, Q. Zhu, X. Xu, H. B. Naveed, X. Sui, J. Xin, L. Zhang, T. Li, K. Zhou, X. Liu, X. Zhan, W. Ma, Adv. Funct. Mater. 2019, 29, 1806804.

[40] A. D. de Zerio, C. Müller, Adv. Energy Mater. 2018, 8, 1702741.

[41] F. Liu, L. Zhou, W. Liu, Z. Zhou, Q. Yue, W. Zheng, R. Sun, W. Liu, S. Xu, H. Fan, L. Feng, Y. Yi, W. Zhang, X. Zhu, Adv. Mater. 2021, 33, 2100830.

[42] N. S. Gobalasingham, S. Noh, J. B. Howard, B. C. Thompson, ACS Appl. Mater. Inter. 2016, 8, 27931.

[43] J. Gao, N. Yu, Z. Chen, Y. Wei, C. Li, T. Liu, X. Gu, J. Zhang, Z. Wei, Z. Tang, X. Hao, F. Zhang, X. Zhang, H. Huang, Adv. Sci. 2022, 9, 2203606.

[44] J. Wan, Z. Chen, L. Zeng, X. Liao, Q. He, S. Liu, P. Zhu, H. Zhu, Y. Chen, J. Energy Chem. 2022, 65, 133.

[45] Y. Chen, P. Ye, X. Jia, W. Gu, X. Xu, X. Wu, J. Wu, F. Liu, Z. Zhu, H. Huang, J. Mater. Chem. A 2017, 5, 19697.

[46] H. Zhang, Y. Lei, H. Wang, W. Wong, J. Mater. Chem. C 2020, 8, 2669.

[47] Q. Lv, X. Wang, W. Yang, K. Wang, C. Xu, M. Zheng, L. Liao, CCS Chem. 2022, 5, 423.

[48] Q. Lv, X. Wang, Y. Yu, M. Zhuo, M. Zheng, L. Liao, Nat. Commun. 2022, 13, 3099.

[49] Y. Lei, Y. Sun, Y. Zhang, H. Zhang, H. Zhang, Z. Meng, W. Wong, J. Yao, H. Fu, Nat. Commun. 2018, 9, 4358.

[50] D. Okada, S. Azzini, H. Nishioka, A. Ichimura, H. Tsuji, E. Nakamura, F. Sasaki, C. Genet, T. W. Ebbesen, Y. Yamamoto, Nano Lett. 2018, 18, 4396.

[51] J. Ravi, A. V. Kumar, D. P. Karothu, M. Annadhasan, P. Naumov, R. Chandrasekar, Adv. Funct. Mater. 2021, 31, 2105415.

[52] A. V. Kumar, M. Godumala, J. Ravi, R. Chandrasekar, Angew. Chem. Int. Ed. 2022, 61, e202212382.

[53] Y. Su, Z. Yao, B. Wu, Y. Zhao, J. Han, J. Sun, M. Zhuo, J. Fan, Z. Wang, J. Pei, L. Liao, X. Wang, Matter 2022, 5, 1520.

[54] Z. Xu, D. Hean, J. Yuan, M. O. Wolf, Chem. Sci. 2022, 13, 6882.

[55] X. Han, Y. Lei, Q. Liao, H. Fu, Angew. Chem. Int. Ed. 2021, 60, 3037.

[56] P. Zhao, L. Zhang, Z. Meng, Y. Lei, Adv. Funct. Mater. 2022, 32, 2205092.

[57] T. Hasell, S. Y. Chong, M. Schmidtmann, D. J. Adams, A. I. Cooper, Angew. Chem. Int. Ed. 2012, 51, 7154.

[58] T. Lu, Q. Chen, J. Comput. Chem. 2022, 43, 539.

[59] H. Hu, F. Meier, D. Zhao, Y. Abe, Y. Gao, B. Chen, T. Salim, E. E. M. Chia, X. Qiao, C. Deibel, Y. M. Lam, Adv. Mater. 2018, 30, 1707621.

[60] S. Yang, D. Wu, W. Gong, Q. Huang, H. Zhen, Q. Ling, Z. Lin, Chem. Sci. 2018, 9, 8975.

[61] F. Liu, T. Zhang, D. Mondal, S. Teng, Y. Zhang, K. Huang, D. Wang, W. Yang, P. Mahadevan, Y. S. Zhao, R. Xie, N. Pradhan, Angew. Chem. Int. Ed. 2021, 60, 13548.

[62] L. Lian, T. Zhang, H. Ding, P. Zhang, X. Zhang, Y. Zhao, J. Gao, D. Zhang, Y. S. Zhao, J. Zhang, ACS Mater. Lett. 2022, 4, 1446.

[63] H. Wang, S. I. Vagin, S. Lane, W. Lin, V. Shyta, W. R. Heinz, C. Van Dyck, A. J. Bergren, K. Gardner, B. Rieger, A. Meldrum, Chem. Mater. 2019, 31, 5816.

[64] B. Zhou, D. Yan, Adv. Funct. Mater. 2019, 29, 1807599.

[65] T. Matsuo, K. Ikeda, S. Hayashi, Aggregate 2023, e378.

[66] X. Tang, L. Cui, H. Li, A. J. Gillett, F. Auras, Y. Qu, C. Zhong, S. T. E. Jones, Z. Jiang, R. H. Friend, L. Liao, Nat. Mater. 2020, 19, 1332.

[67] a) S. Wu, B. Zhou, D. Yan, Adv. Opt. Mater. 2021, 9, 2001768. b) M. Annadhasan, S. Basak, N. Chandrasekhar, R. Chandrasekar, Adv. Opt. Mater. 2020, 8, 2000959.

[68] K. Kokubun, J. Lightwave Technol. 2018, 36, 6.

[69] M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, G. Scalmani, V. Barone, G. A. Petersson, H. Nakatsuji, X. Li, M. Caricato, A. V. Marenich, J. Bloino, B. G. Janesko, R. Gomperts, B. Mennucci, H. P. Hratchian, J. V. Ortiz, A. F. Izmaylov, J. L. Sonnenberg, Williams, F. Ding, F. Lipparini, F. Egidi, J. Goings, B. Peng, A. Petrone, T. Henderson, D. Ranasinghe, et al., Gaussian 16 Rev. C.01, Wallingford, CT, 2016.

[70] a) C. Adamo, V. Barone, J. Chem. Phy. 1999, 110, 6158. b) S. Emamian, T. Lu, H. Kruse, H. Emamian, J. Comput. Chem. 2019, 40, 2868.

[71] K. Momma, F. Izumi, J. Appl. Crystallogr. 2011, 44, 1272.

[72] M. Zhuo, Y. Su, Y. Qu, S. Chen, G. He, Y. Yuan, H. Liu, Y. Tao, X. Wang, L. Liao, Adv. Mater. 2021, 33, 2102719.

RIGHTS & PERMISSIONS

2023 The Authors. Aggregate published by SCUT, AIEI, and John Wiley & Sons Australia, Ltd.