Dual Emission of meso ‐Phenyleneethynylene–BODIPY Oligomers: Synthesis, Photophysics, and Theoretical Optoelectronic Study
| Autor: | Griselda Castruita-de León, J. Reyes Flores, Julio César González-Torres, R. Torres, Gleb Turlakov, Raquel Ledezma, Ivana Moggio, Ronald F. Ziolo, Sagrario M. Montemayor, Eduardo Arias |
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| Rok vydání: | 2020 |
| Předmět: |
010405 organic chemistry
Chemistry Organic Chemistry General Chemistry Nuclear magnetic resonance spectroscopy Chromophore 010402 general chemistry 01 natural sciences Oligomer Catalysis 0104 chemical sciences chemistry.chemical_compound Crystallography Molecule BODIPY Multiplicity (chemistry) Spectroscopy Heteronuclear single quantum coherence spectroscopy |
| Zdroj: | Chemistry – A European Journal. 27:2493-2505 |
| ISSN: | 1521-3765 0947-6539 |
| DOI: | 10.1002/chem.202004481 |
| Popis: | Two series of 2,5-di(butoxy)phenyleneethynylenes, one halogenated (nPEC4-X; n=2, 3, or 4) and the other boron-dipyrromethene (BODIPY) terminated (nPEC4-By; n=3, 4, or 5; By=BODIPY), were synthesized monodirectionally by the step-by-step approach and the molecular structure was corroborated by NMR spectroscopy (1 H, 13 C-DEPTQ-135, COSY, HSQC, HMBC, 11 B, 19 F) and MALDI-TOF mass spectrometry. The multiplicity and J-coupling constants of 1 H, 11 B, and 19 F/11 B NMR signals revealed, in the nPEC4-By series, that the phenyl in the meso position of BODIPY becomes electronically part of the conjugation of the phenyleneethynylene chain, whereas BODIPY is electronically isolated. The photophysical, electrochemical, and theoretical studies confirm this finding because the properties of nPEC4-By are comparable to those of the nPEC4-X oligomers and BODIPY, indicating negligible electron communication between BODIPY and the nPEC4 moieties. Nevertheless, energy transfer (ET) from nPEC4 to BODIPY was rationalized by spectroscopy and theoretical calculations. Its yield decreases with the nPEC4 conjugation length, according to the increase in distance between the two chromophores, resulting in dual emission for the longest oligomer in which ET is quenched. |
| Databáze: | OpenAIRE |
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