Regulation of Multicolor Fluorescence Changes Found in Donor-acceptor-type Mechanochromic Fluorescent Dyes.
benzothiadiazoles
donor-acceptor
mechanochromic fluorescence
multicolor fluorescence
triphenylamines
Journal
Chemistry, an Asian journal
ISSN: 1861-471X
Titre abrégé: Chem Asian J
Pays: Germany
ID NLM: 101294643
Informations de publication
Date de publication:
02 Aug 2021
02 Aug 2021
Historique:
revised:
12
06
2021
received:
19
05
2021
pubmed:
20
6
2021
medline:
15
9
2021
entrez:
19
6
2021
Statut:
ppublish
Résumé
The regulation of multicolor fluorescence changes in mechanochromic fluorescence (MCF) remains a challenging task. Herein, we report the regulation of MCF using a donor-acceptor structure. Two crystal polymorphs, BTD-pCHO(O) and BTD-pCHO(R) produced by the introduction of formyl groups to an MCF dye, respond to a mechanical stimulus, allowing a three-color fluorescence change. Specifically, the orange-colored fluorescence of the metastable BTD-pCHO(O) polymorph changed to a deep-red color in the amorphous-like state to finally give a red color in the stable BTD-pCHO(R) polymorph. This change occurred by mechanical grinding followed by vapor fuming. The two different crystal packing patterns were selectively regulated by the electronic effect of the introduced functional groups. The two types of selectively formed crystals in BTD(F)-pCHO bearing fluorine atoms, and BTD(OMe)-pCHO bearing methoxy groups, respond to mechanical grinding, allowing for the regulation of multicolor MCL from a three-color change to two different types of two-color changes.
Identifiants
pubmed: 34145774
doi: 10.1002/asia.202100538
doi:
Substances chimiques
Fluorescent Dyes
0
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
2136-2145Subventions
Organisme : Kyushu University
Organisme : Cooperative Research Program of Network Joint Research Center
Organisme : Institute for Materials Chemistry and Engineering, Kyushu University
ID : 20202018
Organisme : Institute for Materials Chemistry and Engineering, Kyushu University
ID : 20212012
Informations de copyright
© 2021 Wiley-VCH GmbH.
Références
J. Mei, N. L. C. Leung, R. T. K. Kwok, J. W. Y. Lam, B. Z. Tang, Chem. Rev. 2015, 115, 11718-11940;
Z. Zhao, H. Zhang, J. W. Y. Lam, B. Z. Tang, Angew. Chem. Int. Ed. 2020, 59, 9888-9907;
Angew. Chem. 2020, 132, 9972-9993.
V. K. Praveen, B. Vedhanarayanan, A. Mal, R. K. Mishra, A. Ajayaghosh, Acc. Chem. Res. 2020, 53, 496-507.
E. Lia, K. Jie, M. Liu, X. Sheng, W. Zhua, F. Huang, Chem. Soc. Rev. 2020, 49, 1517-1544.
H. Sun, S. Liu, W. Lin, K. Y. Zhang, W. Lv, X. Huang, F. Huo, H. Yang, G. Jenkins, Q. Zhao, W. Huang, Nat. Commun. 2014, 5, 3601-3609.
K. Y. Zhang, S. Liu, Q. Zhao, W. Huang, Coord. Chem. Rev. 2016, 319, 180-195;
X. Chen, G. Sun, T. Zhang, S. Liu, Q. Zhao, W. Huang, Adv. Mater. 2016, 28, 7137-7142.
M. Irie, T. Fukaminato, T. Sasaki, N. Tamai, T. Kawai, Nature 2002, 420, 759-760;
S.-J. Lim, B.-K. An, S. D. Jung, M.-A. Chung, S. Y. Park, Angew. Chem. Int. Ed. 2004, 43, 6346-6350;
Angew. Chem. 2004, 116, 6506-6510;
J. Su, T. Fukaminato, J.-P. Placial, T. Onodera, R. Suzuki, H. Oikawa, A. Brosseau, F. Brisset, R. Pansu, K. Nakatani, R. Métivier, Angew. Chem. Int. Ed. 2016, 55, 3662-3666;
Angew. Chem. 2016, 128, 3726-3730.
T. Mutai, H. Satou, K. Araki, Nat. Mater. 2005, 4, 685-687.
A. Kishimura, T. Yamashita, K. Yamaguchi, T. Aida, Nat. Mater. 2005, 4, 546-549;
X. Zhu, R. Liu, Y. Li, H. Huang, Q. Wang, D. Wang, X. Zhu, S. Liu, H. Zhu, Chem. Commun. 2014, 50, 12951-12954.
C. Li, X. Tang, L. Zhang, C. Li, Z. Liu, Z. Bo, Y. Q. Dong, Y.-H. Tian, Y. Dong, B. Z. Tang, Adv. Opt. Mater. 2015, 3, 1184-1190;
P. Kumar, J. Dwivedi, B. K. Gupta, J. Mater. Chem. C 2014, 2, 10468-10475.
H. Kobayashi, M. Ogawa, R. Alford, P. L. Choyke, Y. Urano, Chem. Rev. 2010, 110, 2620-2640;
J. Han, K. Burgess, Chem. Rev. 2010, 110, 2709-2728;
Y. Takaoka, A. Ojida, I. Hamachi, Angew. Chem. Int. Ed. 2013, 52, 4088-4106;
Angew. Chem. 2013, 125, 4182-4200;
L. He, B. Dong, Y. Liu, W. Lin, Chem. Soc. Rev. 2016, 45, 6449-6461;
D. Wu, A. C. Sedgwick, T. Gunnlaugsson, E. U. Akkaya, J. Yoon, T. D. James, Chem. Soc. Rev. 2017, 46, 7105-7123;
Y. V. Suseela, N. Narayanaswamy, S. Pratihar, T. Govindaraju, Chem. Soc. Rev. 2018, 47, 1098-1131.
C. Wang, Z. Li, Mater. Chem. Front. 2017, 1, 2174-2194.
Z. Ma, Z. Wang, M. Teng, Z. Xu, X. Jia, ChemPhysChem 2015, 16, 1811-1828.
T. Seki, T. Ozaki, T. Okura, K. Asakura, A. Sakon, H. Uekusa, H. Ito, Chem. Sci. 2015, 6, 2187-2195;
T. Seki, N. Tokodai, S. Omagari, T. Nakanishi, Y. Hasegawa, T. Iwasa, T. Taketsugu, H. Ito, J. Am. Chem. Soc. 2017, 139, 6514-6517;
T. Seki, K. Kobayashi, T. Mashimo, H. Ito, Chem. Commun. 2018, 54, 11136-11139.
J. Guan, F. Xu, C. Tian, L. Pu, M.-S. Yuan, J. Wang, Chem. Asian J. 2019, 14, 216-222;
S. Jiang, J. Wang, Q. Qi, J. Qian, B. Xu, F. Li, Q. Zhou, W. Tian, Chem. Commun. 2019, 55, 3749-3752;
B. Fang, M. Chu, Z. Wu, Y. Shi, Y. S. Zhao, M. Yin, J. Mater. Chem. C 2019, 7, 4434-4440.
Y. Sagara, T. Kato, Nat. Chem. 2009, 1, 605-610.
Z. Chi, X. Zhang, B. Xu, X. Zhou, C. Ma, Y. Zhang, S. Liua, J. Xu, Chem. Soc. Rev. 2012, 41, 3878-3896.
Y. Sagara, S. Yamane, M. Mitani, C. Weder, T. Kato, Adv. Mater. 2016, 28, 1073-1095.
Y. Sagara, T. Kato, Angew. Chem. Int. Ed. 2011, 50, 9128-9132;
Angew. Chem. 2011, 123, 9294-9298.
H. Zhang, Z. Zhang, K. Ye, J. Zhang, Y. Wang, Adv. Mater. 2006, 18, 2369-2372;
Y. Sagara, A. Lavrenova, A. Crochet, Y. C. Simon, K. M. Fromm, C. Weder, Chem. Eur. J. 2016, 22, 4374-4378;
M. Okazaki, Y. Takeda, P. Data, P. Pander, H. Higginbotham, A. P. Monkman, S. Minakata, Chem. Sci. 2017, 8, 2677-2686;
Y. Duan, H. Ma, H. Tian, J. Liu, X. Deng, Q. Peng, Y. Q. Dong, Chem. Asian J. 2019, 14, 864-870.
M.-J. Teng, X.-R. Jia, X.-F. Chen, Y. Wei, Angew. Chem. Int. Ed. 2012, 51, 6398-6401;
Angew. Chem. 2012, 124, 6504-6507;
Z. Ma, M. Teng, Z. Wang, S. Yang, X. Jia, Angew. Chem. Int. Ed. 2013, 52, 12268-12272;
Angew. Chem. 2013, 125, 12494-12498;
Y. Matsunaga, J.-S. Yang, Angew. Chem. Int. Ed. 2015, 54, 7985-7989;
Angew. Chem. 2015, 127, 8096-8100;
H.-J. Kim, D. R. Whang, J. Gierschner, C. H. Lee, S. Y. Park, Angew. Chem. Int. Ed. 2015, 54, 4330-4333;
Angew. Chem. 2015, 127, 4404-4407;
Z. Ma, Z. Wang, X. Meng, Z. Ma, Z. Xu, Y. Ma, X. Jia, Angew. Chem. Int. Ed. 2016, 55, 519-522;
Angew. Chem. 2016, 128, 529-532;
L. Bai, P. Bose, Q. Gao, Y. Li, R. Ganguly, Y. Zhao, J. Am. Chem. Soc. 2017, 139, 436-441.
L.-Y. Hsu, S. Maity, Y. Matsunaga, Y.-F. Hsu, Y.-H. Liu, S.-M. Peng, T. Shinmyozu, J.-S. Yang, Chem. Sci. 2018, 9, 8990-9001.
Y. Dong, B. Xu, J. Zhang, X. Tan, L. Wang, J. Chen, H. Lv, S. Wen, B. Li, L. Ye, B. Zou, W. Tian, Angew. Chem. Int. Ed. 2012, 51, 10782-10785;
Angew. Chem. 2012, 124, 10940-10943;
K. Nagura, S. Saito, H. Yusa, H. Yamawaki, H. Fujihisa, H. Sato, Y. Shimoikeda, S. Yamaguchi, J. Am. Chem. Soc. 2013, 135, 10322-10325;
C. Lv, W. Liu, Q. Luo, H. Yi, H. Yu, Z. Yang, B. Zou, Y. Zhang, Chem. Sci. 2020, 11, 4007-4015;
Q. Luo, L. Li, H. Ma, C. Lv, X. Jiang, X. Gu, Z. An, B. Zou, C. Zhang, Y. Zhang, Chem. Sci. 2020, 11, 6020-6025.
M. Sase, S. Yamaguchi, Y. Sagara, I. Yoshikawa, T. Mutai, K. Araki, J. Mater. Chem. 2011, 21, 8347-8354;
L. Wang, K. Wang, B. Zou, K. Ye, H. Zhang, Y. Wang, Adv. Mater. 2015, 27, 2918-2922;
X. Wu, J. Guo, Y. Cao, J. Zhao, W. Jia, Y. Chen, D. Jia, Chem. Sci. 2018, 9, 5270-5277;
S. Ito, T. Yamada, M. Asami, ChemPlusChem 2016, 81, 1272-1275;
S. Nagai, M. Yamashita, T. Tachikawa, T. Ubukata, M. Asamia, S. Ito, J. Mater. Chem. C 2019, 7, 49883-4998.
Q. Qi, J. Zhang, B. Xu, B. Li, S. X.-A. Zhang, W. Tian, J. Phys. Chem. C 2013, 117, 24997-25003;
R. Li, S. Xiao, Y. Li, Q. Lin, R. Zhang, J. Zhao, C. Yang, K. Zou, D. Lia, T. Yi, Chem. Sci. 2014, 5, 3922-3928;
Y. Sagara, Y. C. Simon, N. Tamaoki, C. Weder, Chem. Commun. 2016, 52, 5694-5697;
Z. Zhao, T. Chen, S. Jiang, Z. Liu, D. Fang, Y. Q. Dong, J. Mater. Chem. C 2016, 4, 4800-4804;
X. Mei, G. Wen, J. Wang, H. Yao, Y. Zhao, Z. Lin, Q. Ling, J. Mater. Chem. C 2015, 3, 7267-7271;
S. Ito, S. Nagai, T. Ubukata, M. Asami, Chem. Lett. 2019, 48, 1492-1495.
H.-J. Kim, J. Gierschner, S. Y. Park, J. Mater. Chem. C 2020, 8, 7417-7421.
Z. He, L. Zhang, J. Mei, T. Zhang, J. W. Y. Lam, Z. Shuai, Y. Q. Dong, B. Z. Tang, Chem. Mater. 2015, 27, 6601-6607;
X. Luo, W. Zhao, J. Shi, C. Li, Z. Liu, Z. Bo, Y. Q. Dong, B. Z. Tang, J. Phys. Chem. C 2012, 116, 21967-21972.
Y. Takeda, T. Kaihara, M. Okazaki, H. Higginbotham, P. Data, N. Tohnai, S. Minakata, Chem. Commun. 2018, 54, 6847-6850.
T. Ishi-i, H. Tanaka, R. Youfu, N. Aizawa, T. Yasuda, S.-i. Kato, T. Matsumoto, New J. Chem. 2019, 43, 4998-5010.
T. Ishi-i, K. Ikeda, Y. Kichise, M. Ogawa, Chem. Asian J. 2012, 7, 1553-1556;
T. Ishi-i, K. Ikeda, M. Ogawa, Y. Kusakaki, RSC Adv. 2015, 5, 89171-89187.
W. Z. Yuan, Y. Tan, Y. Gong, P. Lu, J. W. Y. Lam, X. Y. Shen, C. Feng, H. H.-Y. Sung, Y. Lu, I. D. Williams, J. Z. Sun, Y. Zhang, B. Z. Tang, Adv. Mater. 2013, 25, 2837-2843.
Y. Gong, Y. Tan, J. Liu, P. Lu, C. Feng, W. Z. Yuan, Y. Lu, J. Z. Sun, G. He, Y. Zhang, Chem. Commun. 2013, 49, 400-4011;
Y. Gong, Y. Zhang, W. Z. Yuan, J. Z. Sun, Y. Zhang, J. Phys. Chem. C 2014, 118, 10998-11005;
Y. Zhang, J. Sun, G. Zhuang, M. Ouyang, Z. Yu, F. Cao, G. Pan, P. Tang, C. Zhang, Y. Ma, J. Mater. Chem. C 2014, 2, 195-200.
Y. Zhang, K. Wang, G. Zhuang, Z. Xie, C. Zhang, F. Cao, G. Pan, H. Chen, B. Zou, Y. Ma, Chem. Eur. J. 2015, 21, 2474-2479.
C. Feng, K. Wang, Y. Xu, L. Liu, B. Zou, P. Lu, Chem. Commun. 2016, 52, 3836-3839;
X.-L. Lu, M. Xia, J. Mater. Chem. C 2016, 4, 9350-9358.
S.-J. Yoon, J. W. Chung, J. Gierschner, K. S. Kim, M.-G. Choi, D. Kim, S. Y. Park, J. Am. Chem. Soc. 2010, 132, 13675-13683;
Q. Qi, J. Qian, X. Tan, J. Zhang, L. Wang, B. Xu, B. Zou, W. Tian, Adv. Funct. Mater. 2015, 25, 4005-4010;
S. Yagai, S. Okamura, Y. Nakano, M. Yamauchi, K. Kishikawa, T. Karatsu, A. Kitamura, A. Ueno, D. Kuzuhara, H. Yamada, T. Seki, H. Ito, Nat. Commun. 2014, 5, 4013-4017.
The small internal space in BTD-pCHO(R) seems to be inconsistent with the finding that the crystal density (1.338 g cm−3) of BTD-pCHO(R) is smaller than that (1.358 g cm−3) of BTD-pCHO(O). However, the crystal density is determined by the three-dimensional packing structure. The internal space is focused on the one-dimensional direction. In BTD-pCHO(O) with large internal space, the closely packed structure was found in the two-dimensional direction among the one-dimensional structures (Figure S16d), leading to the large value of crystal density.
C. B. Nielsen, A. J. P. White, I. McCulloch, J. Org. Chem. 2015, 80, 5045-5048.
Y. Yoshii, K. Suenaga, K. Tanaka, Y. Chujo, Chem. Eur. J. 2015, 135, 7231-7237.