Amino-Terephthalonitrile-Based Single Benzene Fluorophores with Large Stokes Shifts and Solvatochromic Behavior.

Publisher: Wiley-VCH Country of Publication: Germany NLM ID: 101294643 Publication Model: Print-Electronic Cited Medium: Internet ISSN: 1861-471X (Electronic) Linking ISSN: 1861471X NLM ISO Abbreviation: Chem Asian J Subsets: PubMed not MEDLINE; MEDLINE

Original Publication: Weinheim, Germany : Wiley-VCH, c2006-

We have synthesized a small library of blue-to-green emissive single benzene-based fluorophores (SBFs) in a short synthetic sequence. The molecules exhibit good Stokes shift in the range of 60-110 nm and select examples also possess very high fluorescence quantum yields of up to 87%. Theoretical investigations into the ground state and excited state geometries of many of these compounds reveal that good degree of planarization between the electron donor secondary amines and electron accepting benzodinitrile units can be achieved under certain solvatochromic conditions, giving rise to the strongly fluorescent behavior. On the other hand, the excited state geometry which lacks co-planarity of the donor amine and the single benzene moiety can open up a non-fluorescent channel. Additionally, in molecules with a dinitrobenzene acceptor, the perpendicular nitro moieties render the molecules completely non-emissive.
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.
C.-T. Chen, Chem. Mater. 2004, 16, 4389-4400;.
L. Yuan, W. Lin, K. Zheng, L. He, W. Huang, Chem. Soc. Rev. 2013, 42, 622-661;.
Q. Zhao, J. Z. Sun, J. Mater. Chem. C 2016, 4, 10588-10609;.
H. Lu, J. Mack, Y. Yang, Z. Shen, Chem. Soc. Rev. 2014, 43, 4778-4823;.
Y. Ni, J. Wu, Org. Biomol. Chem. 2014, 12, 3774-3791;.
Y. Fu, N. S. Finney, RSC Adv. 2018, 8, 29051-29061;.
J.-T. Hou, W. X. Ren, K. Li, J. Seo, A. Sharma, X.-Q. Yu, J. S. Kim, Chem. Soc. Rev. 2017, 46, 2076-2090;.
J. M. An, S. H. Kim, D. Kim, Org. Biomol. Chem. 2020, 18, 4288-4297;.
D. Cao, Z. Liu, P. Verwilst, S. Koo, P. Jangjili, J. S. Kim, W. Lin, Chem. Rev. 2019, 119, 10403-10519;.
H. N. Kim, M. H. Lee, H. J. Kim, J. S. Kim, J. Yoon, Chem. Soc. Rev. 2008, 37, 1465-1472;.
M. Shimizu, T. Hiyama, Chem. Asian J. 2010, 1516-1531.
M. D. Watson, A. Fechtenkotter, K. Mullen, Chem. Rev. 2001, 101, 1267-1300.
 .
H. M. Kim, B. R. Cho, Chem. Rev. 2015, 115, 5014-5055;.
X. Liu, Q. Qiao, W. Tian, W. Liu, J. Chen, M. J. Lang, Z. Xu, J. Am. Chem. 2016, 138, 6960-6963;.
T.-B. Ren, W. Xu, W. Zhang, X.-X. Zhang, Z.-Y. Wang, Z. Xiang, L. Yuan, X.-B. Zhang, J. Am. Chem. Soc. 2018, 140, 7716-7722.
 .
X. Ma, R. Sun, J. Cheng, J. Liu, F. Gou, H. Xiang, X. Zhou, J. Chem. Educ. 2016, 93, 345-350;.
Y. Hong, J. Lam, B. Tang, Chem. Soc. Rev. 2011, 40, 5361-5388.
A. P. Demchenko, Methods Appl. Fluoresc. 2020, 8, 022001.
J. Kim, J. H. Oha, D. Kim, Org. Biomol. Chem. 2021, 19, 933-946.
 .
R. Huang, B. Liu, C. Wang, Y. Wang, H. Zhang, J. Phys. Chem. C. 2018, 122, 10510-10518;.
R. Huang, B. Tang, K. Ye, C. Wang, H. Zhang, Adv. Opt. Mater. 2019, 7, 1900927;.
B. Tang, C. Wang, Y. Wang, H. Zhang, Angew. Chem. Int. Ed. 2017, 129, 12717-12721;.
H. Liu, S. Zhang, L. Ding, Y. Fang, Chem. Commun. 2021, 3, 4011-4014;.
E. Cho, J. Choi, S. Jo, D. H. Park, Y. K. Hong, D. Kim, T. S. Lee, ChemPlusChem. 2019, 84, 1130-1134;.
X. Zhang, J. Wang, F. Yu, X. Cheng, Y. Hao, Y. Liu, X. Huang, H. Hao, CrystEngComm. 2022, 24, 854-862;.
G. Yin, Y. Li, S. Li, B. Xu, Q. Yang, Y. Zhang, J. Zhao, X. Cao, Dyes Pigm. 2022, 198, 110013;.
M. Mandal, T. Chatterjee, D. Roy, A. Das, C. K. De, S. Mandal, S. Ghosh, A. Sen, M. Ta, P. K. Mandal, J. Phys. Chem. C 2020, 124, 27049-27054;.
B. Liu, Q. Di, W. Liu, C. Wang, Y. Wang, H. Zhang, J. Phys. Chem. Lett. 2019, 10, 1437-1442;.
H. Liu, S. Yan, R. Huang, Z. Gao, G. Wang, L. Ding, Y. Fang, Chem.-Eur. J. 2019, 25, 16732-16739;.
B. Tang, C. Wang, Y. Wang, H. Zhang, Angew. Chem. Int. Ed. 2017, 56, 12543-12547;.
Angew. Chem. 2017, 129, 12717-12721.
A. Baeyer, Ber. Dtsch. Chem. Ges. 1886, 19, 428-433.
Y. Zhao, H. Gao, Y. Fan, T. Zhou, Z. Su, Y. Liu, Y. Wang, Adv. Mater. 2009, 21, 3165-3169.
M. Shimizu, Y. Asai, Y. Takeda, A. Yamatani, T. Hiyama, Tetrahedron Lett. 2011, 52, 4084-4089.
T. Beppu, K. Tomiguchi, A. Masuhara, Y.-J. Pu, H. Katagiri, Angew. Chem. Int. Ed. 2015, 54, 7332-7335;.
Angew. Chem. 2015, 127, 7440-7443.
Z. Xiang, Z.-Y. Wang, T.-B. Ren, W. Xu, Y.-P. Liu, X.-X. Zhang, P. Wu, L. Yuan, X.-B. Zhang, Chem. Commun. 2019, 55, 11462-11465.
M. Mandal, T. Chatterjee, A. Das, S. Mandal, A. Sen, M. Ta, P. K. Mandal, J. Phys. Chem. C 2019, 123, 24786-24792.
A. A. Phadte, A. Chattopadhyay, S. Banerjee, D. S. Sisodiya, T. Raghava, ChemistrySelect 2020, 5, 10177-10186.
S. Banerjee, A. Chattopadhyay, A. Banerjee, M. Haridas, M. Das, M. S. Majik, Y. Mauyra-Kr, Bioorg. Med. Chem. Lett. 2015, 25, 753-757.
R. Chen, H. Ye, T. Fang, S. Liu, L. Yi, L. Cheng, Org. Biomol. Chem. 2022, 20, 4128-4134.
N. Castillo, F. Matta, R. J. Boyd, J. Chem. Inf. Model. 2005, 45, 354-359.
X.-F. Zhang, X. Li, J. Lumin. 2011, 131, 2263-2266.
 .
R. Cammi, B. Mennucci, J. Tomasi, J. Phys. Chem. A. 2000, 104, 5631-37;.
M. Cossi, V. Barone, J. Chem. Phys. 2001, 115, 4708-17;.
C. Jamorski, M. E. Casida, D. R. Salahub, J. Phys. Chem. 1996, 104, 5134-5147;.
R. Bauerschmitt, R. Alrichs, Chem. Phys. Lett. 1996, 256, 454-464;.
R. Bauerschmitt, M. Häser, O. Treutler, R. Alrichs, Chem. Phys. Lett. 1997, 264, 573-578.
M. Cossi, N. Rega, G. Scalmani, V. Barone, J. Comb. Chem. 2003, 24, 669-681.
 .
Meng-Chi Chen, Deng-Gao Chen, Pi-Tai Chou, ChemPlusChem.(86) 11-27;.
C.-K. Lin, Y.-F. Wang, Y.-C. Cheng, J.-S. Yang, J. Phys. Chem. A. 2013, 117, 3158-3164;.
R. Ghosh, D. K. Palit, J. Phys. Chem. A. 2012, 116, 1993-2005;.
S. A. Kovalenko, R. Schanz, V. M. Farztdinov, H. Hennig, N. P. Ernsting, Chem. Phys. Lett. 2000, 323, 312-322;.
V. M. Farztdinov, R. Schanz, S. A. Kovalenko, N. P. Ernsting, J. Phys. Chem. A. 2000, 104, 11486-11496;.
S. Rafiq, R. Yadav, P. Sen, J. Phys. Chem. A. 2011, 115, 8335-8343;.
J.-M. Mewes, V. Jovanović, C. M. Marian, A. Dreuw, Phys. Chem. Chem. Phys. 2014, 16, 12393-12406;.
J. P. Zobel, J. J. Nogueira, L. González, Chem. Eur. J. 2018, 24, 5379-5387.
K.-I. Oh, K. Rajesh, J. F. Stanton, C. R. Baiz, Angew. Chem. Int. Ed. 2017, 56, 11375-11379;.
Angew. Chem. 2017, 129, 11533-11537.
 .
A. Tarai, Y. Li, B. Liu, D. Zhang, J. Li, W. Yan, J. Zhang, J. Qu, Z. Yang, Coord. Chem. Rev. 2021, 445, 214070;.
G. Rim, G. Jin, S. Ah, K. Young, C. Kim, Sensors Actuators B. Chem. 2015, 215, 188-195.
B. Zhao, T. Liu, Y. Fang, L. Wang, B. Song, Q. Deng, Tetrahedron Lett. 2016, 57, 4417-4423.
M. H. Gehlen, Journal Photochem. Photobiol. C Photochem. Rev. 2020, 42, 100338.

Central Sophisticated Instrumentation Facility (CSIF); BITS Pilani KK Birla Goa Campus

Keywords: TDDFT; amino-terephthalonitrile; push-pull compounds; single benzene fluorophores; solvatochromism

Date Created: 20230309 Date Completed: 20230417 Latest Revision: 20230417

20250114

10.1002/asia.202201314

36892161