Skip to main content
SpringerLink
Log in

The isomeric effect on the D-π-π-A prototype fluorescent material: synthesis, photophysical property, and computation

  • Original Paper
  • Published:
Monatshefte für Chemie - Chemical Monthly Aims and scope Submit manuscript

Abstract

Two novel organic fluorescent isomers with D-π-π-A prototype structure, namely, (E)-2-[3-([1,1'-biphenyl]-4-yl)-1-(6-methoxynaphthalen-2-yl)allylidene]malononitrile and (E)-2-[1-([1,1'-biphenyl]-4-yl)-3-(6-methoxynaphthalen-2-yl)allylidene]malononitrile, were synthesized. Due to the exchange of naphthalene and biphenyl moieties on each side of conjugated bridge (C = C(CN)2)-conjugated bridge (C = C) group, two compounds are organic fluorescent isomers, and display different molecular stacking mode and photophysical property. Molecules of (E)-2-[3-([1,1'-biphenyl]-4-yl)-1-(6-methoxynaphthalen-2-yl)allylidene]malononitrile are packed with H-aggregation, while (E)-2-[1-([1,1'-biphenyl]-4-yl)-3-(6-methoxynaphthalen-2-yl)allylidene]malononitrile has a J-aggregation. Both of two compounds show solvatochromism and tunable aggregation-induced enhanced emission property.

Graphic abstract

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Fig. 1
Fig. 2
Fig. 3
Fig. 4
Fig. 5
Fig. 6
Fig. 7
Fig. 8
Fig. 9
Fig. 10
Fig. 11
Fig. 12
Fig. 13

Similar content being viewed by others

References

  1. Wang JM, Zhang PF, Cheng JG, Wang Y, Ma LL, Yang GP, Wang YY (2021) CrystEngComm 23:411

    Article  CAS  Google Scholar 

  2. Tonga M (2021) New J Chem 45:23

    Article  CAS  Google Scholar 

  3. Chen H, Sun H, Zhang W, Zhang Q, Ma J, Li Q, Guo X, Xu K, Tang Y (2021) New J Chem 45:28

    Article  CAS  Google Scholar 

  4. Pallavi P, Kumar V, Hussain MDW, Patra A (2018) ACS Appl Matter Interfaces 10:44696

    Article  CAS  Google Scholar 

  5. Guo SM, Zhang YY, Huang JY, Kong L, Yang JX (2021) CrystEngComm 23:221

    Article  CAS  Google Scholar 

  6. Wu Q, Zhang T, Peng Q, Wang D, Shuai Z (2014) Phys Chem Chem Phys 16:5545

    Article  CAS  Google Scholar 

  7. Jiro M, Zhu F, Yoshinori N, Hiromu A (2008) Spectrochim Acta Part A 69:167

    Article  CAS  Google Scholar 

  8. Palakollu V, Kanvah S (2014) New J Chem 38:5736

    Article  CAS  Google Scholar 

  9. Li YX, Chen Z, Cui Y, Xia GM, Yang XF (2012) J Phys Chem C 116:6401

    Article  CAS  Google Scholar 

  10. Shao B, Jin R, Li A, Liu Y, Li B, Xu S, Xu W, Xu B, Tian W (2019) J Mater Chem C 7:3263

    Article  CAS  Google Scholar 

  11. Dong YJ, Zhang JB, Tian X, Wang LJ, Chen JL, Li B, Ye L, Xu B, Zhou B, Tian WJ (2013) J Mater Chem C 1:7553

    Google Scholar 

  12. Mei J, Leung NLC, Lam RTK, Tang JWY (2015) Chem Rev 115:11718

    Article  CAS  Google Scholar 

  13. Feng GX, Liu B (2018) Acc Chem Res 51:1404

    Article  CAS  Google Scholar 

  14. Gan Z, Liu Y, Wang L, Jiang SQ, Xia N, Yan ZP, Wu X, Zhang JR, Gu WM, He LZ, Dong JW, Ma XD, Kim J, Wu ZY, Xu YX, Li YC, Wu ZK (2020) Nat Commun 11:5572

    Article  CAS  Google Scholar 

  15. Zhang X, Wang H, Li D, Chen M, Mao Y, Du B, Zhuang Y, Tan W, Huang W, Zhao Y, Wang T (2020) Macromolecules 10:3737

    Google Scholar 

  16. Koh CW, Cho HW, Rashid MAM, Lee TH, Park SY, Lee W, Kwak K, Kim JY, Woo HY (2020) Adv Mater Technol 5:2000174

    Article  CAS  Google Scholar 

  17. Zhang GB, Li Z, Chen FJ, Zhang DT, Ji WH, Yang ZP, Wu Q, Zhang CW, Li L, Huang W (2020) J Innov Opt Health Sci 03:2050013

    Article  Google Scholar 

  18. Niu C, You Y, Zhao L, He D, Na N, Ouyang J (2015) Chem Eur J 21:13983

    Article  CAS  Google Scholar 

  19. Wu DE, Wang MN, Luo YH, Zhang YW, Ma YH, Sun BW (2017) New J Chem 41:4220

    Article  CAS  Google Scholar 

  20. Zhang Q, Yu P, Fan Y, Sun C, He H, Liu X, Lu L, Zhao M, Zhang H, Zhang F (2020) Angew Chem Int Ed 59:1

    Article  CAS  Google Scholar 

  21. Choi S, Bouffard J, Kim Y (2014) Chem Sci 5:751

    Article  CAS  Google Scholar 

  22. Wang Y, Liu T, Bu L, Li J, Yang C, Li X, Tao Y, Yang W (2012) J Phys Chem C 116:15576

    Article  CAS  Google Scholar 

  23. Yan YY, Xu SD, Cheng XM, Cai XL, Liu B (2016) Angew Chem 128:6567

    Article  Google Scholar 

  24. Sheldrick GM (2015) Acta Crystallogr C 71:3

    Article  CAS  Google Scholar 

  25. Brandenburg K (2006) DIAMOND, Version 3.1b, crystal and molecular structure visualization. Crystal impact GbR. Bonn, Germany

    Google Scholar 

  26. Mercury 2.3 (2003) Supplied with Cambridge structure database. CCDC, Cambridge, UK

    Google Scholar 

  27. Frisch MJ, Trucks GW, Schlegel HB, Scuseria GE, Robb MA, Cheeseman JR, Montgomery JA Jr, Vreven T, Kudin KN, Burant JC, Millam JM, Iyengar SS, Tomasi J, Barone V, Mennucci B, Cossi M, Scalmani G, Rega N, Petersson GA, Nakatsuji H, Hada M, Ehara M, Toyota K, Fukuda R, Hasegawa J, Ishida M, Nakajima T, Honda Y, Kitao O, Nakai H, Klene M, Li X, Knox JE, Hratchian HP, Cross JB, Adamo C, Jaramillo J, Gomperts R, Stratmann RE, Yazyev O, Austin AJ, Cammi R, Pomelli C, Ochterski JW, Ayala PY, Morokuma K, Voth GA, Salvador P, Dannenberg JJ, Zakrzewski VG, Dapprich S, Daniels AD, Strain MC, Farkas O, Malick DK, Rabuck AD, Raghavachari K, Foresman JB, Ortiz JV, Cui Q, Baboul AG, Clifford S, Cioslowski J, Stefanov BB, Liu G, Liashenko A, Piskorz P, Komaromi I, Martin RL, Fox DJ, Keith T, Al-Laham MA, Peng CY, Nanayakkara A, Challacombe M, Gill PMW, Johnson B, Chen W, Wong MW, Gonzalez C, Pople JA (2003) Gaussian 03, Revision A.1. Gaussian Inc, Pittsburgh, PA

    Google Scholar 

Download references

Acknowledgements

This work has been supported by the Natural Science Foundation of the Jiangsu Higher Education Institutions of China (Project 19KJB150021), Research Fund Project of Changzhou Vocational Institute of Engineering (Project 11130300118010), Qinglan Project of Jiangsu Province; National Vocational Education Teacher Teaching innovation Team Consruction Project (Project 360A10-04-2019-0017-1/1-72) and Research Foundation for Advanced Talents of Changzhou Vocational Institute of Engineering (Project 11130900118004).

Author information

Authors and Affiliations

  1. School of Chemical Engineering and Pharmacy, Changzhou Vocational Institute of Engineering, Changzhou, 213164, People’s Republic of China

    Dong-En Wu, Qing-Hui Guo, Qiwei Qiao, Yu-Jie Cai & Qing-Qing Zhou

Authors
  1. Dong-En Wu
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Qing-Hui Guo
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Qiwei Qiao
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Yu-Jie Cai
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Qing-Qing Zhou
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Qiwei Qiao.

Additional information

Publisher's Note

Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.

Supplementary Information

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Wu, DE., Guo, QH., Qiao, Q. et al. The isomeric effect on the D-π-π-A prototype fluorescent material: synthesis, photophysical property, and computation. Monatsh Chem 152, 1315–1326 (2021). https://doi.org/10.1007/s00706-021-02846-z

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s00706-021-02846-z

Keywords

Search

Navigation