Prediction of Second-Order Nonlinear Optical Properties of D–π–A Compounds Containing Novel Fluorene Derivatives: A Promising Route to Giant Hyperpolarizabilities

  • Muhammad Usman Khan
  • Muhammad IbrahimEmail author
  • Muhammad KhalidEmail author
  • Ataualpa Albert Carmo Braga
  • Sarfraz Ahmed
  • Ayesha Sultan
Original Paper


Herein, first attempt has been made to utilize fluorene-based dye-sensitized solar cell (DSSCs) dye JK-201 as potential nonlinear optical (NLO) material and for the theoretical designing of novel NLO chromophores JK-D1–JK-D12. DFT/TDDFT calculations were performed to compute the effect of π-linkers and acceptors-steered modulation on electronic, photophysical and NLO properties of JK-201 and JK-D1–JK-D12. Results illustrate that computed λmax (484.74 nm) and experimentally calculated λmax (481 nm) of JK-201 was found in good agreement. Maximum red shifted absorption spectrum was observed in JK-D12 with 599.38 nm. JK-D1–JK-D12 showed narrow energy gap and broader absorption spectrum as compared to JK-201. NBO analysis confirmed the formation of charge separation state due to robust range of electrons/charge transfer from donor to acceptor via π-bridge. Giant NLO response was observed in all compounds. Particularly, JK-D12 displayed surprisingly large 〈α〉 and βtot computed 1376.74 (a.u.) and 405,731.84 (a.u.) respectively. Although literature is flooded with D–π–A compounds investigated for their DSSCs properties, but research reports on their NLO properties and utilization as NLO materials are completely deserted. Our research will open new horizons to explore DSSCs materials for NLO applications. This theoretical framework also exposed that fluorene-substituted chromophores are excellent NLO candidates for modern hi-tech applications.

Graphical Abstract


NLO response properties D–π–A organic chromophores Density functional theory Molecular modeling π-Conjugated linkers Acceptor units 



Ataualpa A. C. Braga, (Grants # 2011/07895-8, 2015/01491-3 and 2014/25770-6) is thankful to Fundação de Amparo à Pesquisa do Estado de São Paulo for financial support. AACB (Grant 309715/2017-2) also thanks the Brazilian National Research Council (CNPq) for financial support and fellowships. This study was financed in part by the Coordenação de Aperfeiçoamento de Pessoal de Nível Superior—Brasil (CAPES)—Finance Code 001.

Compliance with Ethical Standards

Conflict of interest

The authors declare that they have no conflict of interests.

Associated Content

Optimized Cartesian coordinates of our studied compounds are available in supporting information file.

Supplementary material

10876_2018_1489_MOESM1_ESM.docx (79 kb)
Supplementary material 1 (DOCX 79 kb)


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Copyright information

© Springer Science+Business Media, LLC, part of Springer Nature 2019

Authors and Affiliations

  • Muhammad Usman Khan
    • 1
  • Muhammad Ibrahim
    • 1
    Email author
  • Muhammad Khalid
    • 2
    Email author
  • Ataualpa Albert Carmo Braga
    • 3
  • Sarfraz Ahmed
    • 2
  • Ayesha Sultan
    • 4
  1. 1.Department of Applied ChemistryGovernment College UniversityFaisalabadPakistan
  2. 2.Department of ChemistryKhwaja Fareed University of Engineering and Information TechnologyRahim Yar KhanPakistan
  3. 3.Departamento de Química Fundamental, Instituto de QuímicaUniversidade de São PauloSão PauloBrazil
  4. 4.Department of ChemistryUniversity of Education LahoreFaisalabadPakistan

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