Linear push–pull chromophores with tunable acceptor strength for organic opto-electronics

Abstract

This work focuses on the influence of the electron-withdrawing character of acceptor units on both the molecular and macroscopic properties of thiophene (T)-bridged push–pull donor–π–acceptor chromophores with tetrahydroquinoline (TQ) as donor. The acceptors are based on tricyanovinylene (TCV), double fluorinated indanone (2FIC) and two tricyanodihydrofuran-based frameworks TCF(Me,Me) and TCF(Ph,CF3). Crystal structure and vibrational spectroscopy show that TCV and 2FIC lead to the strongest degree of polarization of the ground-state, while optical and electrochemical characterization reveal the lowest gap for TCF(Ph,CF3). DFT calculations support the experimental findings. Optical studies and thin film morphological studies show distinct differences in their as-cast state and upon thermal annealing. While TQ-T-2FIC and TQ-T-TCV exhibit a hypsochromic (blue) shift of the main absorption band from solution to film due to H-aggregation, the TCF derivatives show a broadening and a bathochromic (red) shift of the absorption band indicative of a more disordered, amorphous morphology. Subsequent thermal annealing of the TQ-T-TCV and TQ-T-TCF(Me,Me) films drives a further molecular reorganization, enhancing structural order and resulting in a pronounced blue-shift of the absorption band. These findings show the potential applicability of the chromophores for organic photovoltaics and electro-optic applications.

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Cite

BibTeX RIS

BibTeX

@article{großmann2026linear,
  title = {{Linear push–pull chromophores with tunable acceptor strength for organic opto-electronics}},
  author = {Dennis Großmann and David Gepperth and Sergio Gámez-Valenzuela and Irene Badia Domínguez and Wolfgang Frey and Magali Allain and Pedro Resende and Matthias Schwartzkopf and Klaus Dirnberger and Philippe Blanchard and Chris Mcneill and M. Carmen Ruiz Delgado and Sabine Ludwigs},
  journal = {Journal of Materials Chemistry C},
  year = {2026},
  month = nov,
  doi = {10.1039/d6tc02162j},
  url = {https://hal.science/hal-05847244v1},
  note = {CC BY 4.0},
}

RIS

TY  - JOUR
TI  - Linear push–pull chromophores with tunable acceptor strength for organic opto-electronics
AU  - Dennis Großmann
AU  - David Gepperth
AU  - Sergio Gámez-Valenzuela
AU  - Irene Badia Domínguez
AU  - Wolfgang Frey
AU  - Magali Allain
AU  - Pedro Resende
AU  - Matthias Schwartzkopf
AU  - Klaus Dirnberger
AU  - Philippe Blanchard
AU  - Chris Mcneill
AU  - M. Carmen Ruiz Delgado
AU  - Sabine Ludwigs
PY  - 2026
DA  - 2026/11/01
JO  - Journal of Materials Chemistry C
DO  - 10.1039/d6tc02162j
UR  - https://hal.science/hal-05847244v1
AB  - This work focuses on the influence of the electron-withdrawing character of acceptor units on both the molecular and macroscopic properties of thiophene (T)-bridged push–pull donor–π–acceptor chromophores with tetrahydroquinoline (TQ) as donor. The acceptors are based on tricyanovinylene (TCV), double fluorinated indanone (2FIC) and two tricyanodihydrofuran-based frameworks TCF(Me,Me) and TCF(Ph,CF3). Crystal structure and vibrational spectroscopy show that TCV and 2FIC lead to the strongest degree of polarization of the ground-state, while optical and electrochemical characterization reveal the lowest gap for TCF(Ph,CF3). DFT calculations support the experimental findings. Optical studies and thin film morphological studies show distinct differences in their as-cast state and upon thermal annealing. While TQ-T-2FIC and TQ-T-TCV exhibit a hypsochromic (blue) shift of the main absorption band from solution to film due to H-aggregation, the TCF derivatives show a broadening and a bathochromic (red) shift of the absorption band indicative of a more disordered, amorphous morphology. Subsequent thermal annealing of the TQ-T-TCV and TQ-T-TCF(Me,Me) films drives a further molecular reorganization, enhancing structural order and resulting in a pronounced blue-shift of the absorption band. These findings show the potential applicability of the chromophores for organic photovoltaics and electro-optic applications.
SN  - 2050-7526
SN  - 2050-7534
ER  -

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