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Peer-reviewedCC BY 4.0ACS Omega

Platform Synthesis for the Rapid Construction of V-Shaped and Cruciform Push–Pull Compounds

  • Pratiksha Gawas1
  • Angelo Martinelli1
  • Giovanni Preda1
  • Alessio Orbelli Biroli1
  • Elisavet Tatsi2
  • Chiara Botta3
  • Francesco Porcelli4
  • Giuseppe Mattioli4
  • Gianmarco Griffini2
  • Andrea Nitti1
  • Dario Pasini1
4 affiliations
  1. 1University of Pavia , , Via Taramelli 12 , ,
  2. 2Politecnico di Milano , , Piazza Leonardo da Vinci 32 , ,
  3. 3Institute of Sciences and Chemical Technologies “Giulio Natta” (SCITEC) of CNR , via Corti 12 , ,
  4. 4CNR-Istituto di Struttura della Materia (CNR-ISM) , ,
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Abstract

We report the modular synthesis of cruciform push–pull compounds from V-shaped di- and trisubstituted thiophenes obtained from commercially available 2,3-dibromothiophene (DBT) via sequential couplings using the concept of “platform synthesis”. Orthogonal C2/C3 functionalization with EDOT-and naphthothiophene-based molecular modules yielded a library of 8 V-shaped, sterically hindered π-conjugated derivatives. Coupling in C5 with electron-deficient benzothiadiazole units, to complete the “platform” synthetic sequence, afforded two different “cruciform-like” push–pull luminophores emitting in the deep red region of the visible spectrum. Photophysical and electrochemical studies, supported by calculations, revealed that the substitution pattern on DBT is crucial in tuning both emission efficiency and the bathochromic shifts, inducing aggregation-induced enhanced emission (AIEE) in one derivative. This work highlights the versatility of platform synthesis in the realization of relevant materials for optoelectronic applications.

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Cite

BibTeXRIS
BibTeX
@article{gawas2026platform,
  title = {{Platform Synthesis for the Rapid Construction of V-Shaped and Cruciform Push–Pull Compounds}},
  author = {Pratiksha Gawas and Angelo Martinelli and Giovanni Preda and Alessio Orbelli Biroli and Elisavet Tatsi and Chiara Botta and Francesco Porcelli and Giuseppe Mattioli and Gianmarco Griffini and Andrea Nitti and Dario Pasini},
  journal = {ACS Omega},
  year = {2026},
  month = nov,
  doi = {10.1021/acsomega.6c08890},
  url = {https://pubs.acs.org/acsodf/article/doi/10.1021/acsomega.6c08890/5462088/Platform-Synthesis-for-the-Rapid-Construction-of-V},
  note = {CC BY 4.0},
}
RIS
TY  - JOUR
TI  - Platform Synthesis for the Rapid Construction of V-Shaped and Cruciform Push–Pull Compounds
AU  - Pratiksha Gawas
AU  - Angelo Martinelli
AU  - Giovanni Preda
AU  - Alessio Orbelli Biroli
AU  - Elisavet Tatsi
AU  - Chiara Botta
AU  - Francesco Porcelli
AU  - Giuseppe Mattioli
AU  - Gianmarco Griffini
AU  - Andrea Nitti
AU  - Dario Pasini
PY  - 2026
DA  - 2026/11/02
JO  - ACS Omega
DO  - 10.1021/acsomega.6c08890
UR  - https://pubs.acs.org/acsodf/article/doi/10.1021/acsomega.6c08890/5462088/Platform-Synthesis-for-the-Rapid-Construction-of-V
AB  - We report the modular synthesis of cruciform push–pull compounds from V-shaped di- and trisubstituted thiophenes obtained from commercially available 2,3-dibromothiophene (DBT) via sequential couplings using the concept of “platform synthesis”. Orthogonal C2/C3 functionalization with EDOT-and naphthothiophene-based molecular modules yielded a library of 8 V-shaped, sterically hindered π-conjugated derivatives. Coupling in C5 with electron-deficient benzothiadiazole units, to complete the “platform” synthetic sequence, afforded two different “cruciform-like” push–pull luminophores emitting in the deep red region of the visible spectrum. Photophysical and electrochemical studies, supported by calculations, revealed that the substitution pattern on DBT is crucial in tuning both emission efficiency and the bathochromic shifts, inducing aggregation-induced enhanced emission (AIEE) in one derivative. This work highlights the versatility of platform synthesis in the realization of relevant materials for optoelectronic applications.
SN  - 2470-1343
ER  -