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Tuning the Properties of Donor-Acceptor and Acceptor-Donor-Acceptor Boron Difluoride Hydrazones via Extended π-Conjugation.
| Content Provider | Europe PMC |
|---|---|
| Author | Cappello, Daniela Buguis, Francis L. Gilroy, Joe B. |
| Copyright Year | 2022 |
| Abstract | Molecular materials with π-conjugated donor–acceptor(D–A) and acceptor–donor–acceptor (A–D–A)electronic structures have received significant attention due to theirusage in organic photovoltaic materials, in organic light-emittingdiodes, and as biological imaging agents. Boron-containing molecularmaterials have been explored as electron-accepting units in compoundswith D–A and A–D–A properties as they often exhibitunique and tunable optoelectronic and redox properties. Here, we utilizeStille cross-coupling chemistry to prepare a series of compounds withboron difluoride hydrazones (BODIHYs) as acceptors and benzene, thiophene,or 9,9-dihexylfluorene as donors. BODIHYs with D–A and A–D–Aproperties exhibited multiple reversible redox waves, solid-stateemission with photoluminescence quantum yields up to 10%, and aggregation-inducedemission (AIE). Optical band gaps (or highest occupied molecular orbital(HOMO)–lowest unoccupied molecular orbital (LUMO) gaps) determinedfor these compounds (2.02–2.25 eV) agree well with those determinedfrom cyclic voltammetry experiments (2.05–2.42 eV). The optoelectronicproperties described herein are rationalized with density functionaltheory calculations that support the interpretation of the experimentalfindings. This work provides a foundation of understanding that willallow for the consideration of D–A and A–D–ABODIHYs to be incorporated into applications (e.g., organic electronics) where fine-tuning of band gaps is required. |
| Journal | ACS Omega |
| Volume Number | 7 |
| PubMed Central reference number | PMC9476501 |
| Issue Number | 36 |
| PubMed reference number | 36120012 |
| e-ISSN | 24701343 |
| DOI | 10.1021/acsomega.2c04401 |
| Language | English |
| Publisher | American Chemical Society |
| Publisher Date | 2022-08-26 |
| Access Restriction | Open |
| Rights License | Permits the broadest form of re-use including for commercial purposes, provided that author attribution and integrity are maintained (https://creativecommons.org/licenses/by/4.0/). © 2022 The Authors. Published by American Chemical Society |
| Content Type | Text |
| Resource Type | Article |
| Subject | Chemistry Chemical Engineering |
