Spectroscopic Investigation and Theoretical Modeling of Benzothiadiazole-Based Charge-Transfer Chromophores: From Solution to Nanoaggregates
Abstract
Experimental and theoretical investigations are presented on four quadrupolar molecules constituted of a central electron-acceptor 2,1,3-benzothiadiazole conjugated at both sides with electron-donating thiophene (or 2,2′-bithiophene) substituted groups. Previous investigation of their physicochemical properties demonstrated that thermally induced self-organization might be achieved for one of them. In this study, we further explore the structure–properties relationships for these quadrupolar chromophores also examining their aggregation behavior in organic nanoparticles. Strong spectroscopic evidence of J-aggregates formation is obtained, favored by the presence of branched terminal alkyl chains. The surprisingly low fluorescence quantum yield of these J-aggregates is rationalized within the essential-state model approach.
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A V-shaped D-A-D system composed of benzothiadiazole and two electron-donating thiophene (or bithiophene) units formed a dark state associated with an intermediate aggregate form, which was responsible for the observed fluorescence quenching.
“Unlike J-aggregates assembled from benzothiadiazole-based charge-transfer complexes, a V-shaped D-A-D system composed of benzothiadiazole and two electron-donating thiophene (or bithiophene) units formed a dark state associated with an intermediate aggregate form, which was responsible for the observed fluorescence quenching.127”
From The Pursuit of Shortwave Infrared-Emitting Nanoparticles with Bright Fluorescence through Molecular Design and Excited-State Engineering of Molecular Aggregates (2022) · cites this paper as [127]
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Imaging macrophages with nanoparticles
Weissleder, R., Nahrendorf, M., & Pittet, M. J. (2014) · Nature Materials · doi:10.1038/nmat3780 · Cited by 809 · see citing works
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Piwoński, H., Nozue, S., & Habuchi, S. (2022) · ACS Nanoscience Au · doi:10.1021/acsnanoscienceau.1c00038 · Cited by 39 · see citing works
- Authors
- Bardi, B., Dall’Agnese, C., Moineau-Chane Ching, K. I., Painelli, A., & Terenziani, F.
- Affiliations
- University of Parma (IT)
- Centre National de la Recherche Scientifique (FR)
- CNRS, LCC (Laboratoire de Chimie de Coordination), 205 route de Narbonne, F-31077 Toulouse, France
- Corresponding author
- Terenziani, Francesca
- Venue
- The Journal of Physical Chemistry C
- Publisher
- American Chemical Society (ACS)
- Published
- 2017-08-03
- Volume
- 121
- Issue
- 32
- Pages
- 17466-17478
- ISSN
- 1932-7447 (ISSN-L)
- 1932-7455
- OpenAlex
- W2738796202
- Cited by
- 30
- References
- 1
- Citations by year
- 2026: 1 · 2025: 1 · 2024: 1 · 2023: 6 · 2022: 4 · 2021: 7 · 2020: 3 · 2019: 6 · 2018: 1
- FWCI
- 2.01
- Type
- journal article
- Language
- en
- Open access
- closed
- Locations
- The Journal of Physical Chemistry C (publishedVersion)
- HAL (submittedVersion)
- Funders
- Ministero dell???Istruzione, dell???Universit?? e della Ricerca (2012T9XHH7, RBFR10Y5VW)
- China Scholarship Council
- Topics
- Physical Sciences › Chemistry › Physical and Theoretical Chemistry › Photochemistry and Electron Transfer Studies
- Physical Sciences › Materials Science › Materials Chemistry › Luminescence and Fluorescent Materials
- Physical Sciences › Physics and Astronomy › Atomic and Molecular Physics, and Optics › Spectroscopy and Quantum Chemical Studies
- Keywords
- benzothiadiazole, charge-transfer chromophores, J-aggregates, self-organization, organic nanoparticles, aggregation behavior, thiophene, bithiophene, quadrupolar molecules, fluorescence quantum yield, structure-property relationships, branched alkyl chains
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