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Cited by 111Luminescence and Fluorescent MaterialsMolecular Sensors and Ion DetectionPhotochemistry and Electron Transfer Studies

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Domino-like multi-emissions across red and near infrared from solid-state 2-/2,6-aryl substituted BODIPY dyes

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Tian, Dan, Qi, Fen, Ma, Huili, Wang, Xiaoqing, Pan, Yue, Chen, Runfeng, Shen, Zhen, Liu, Zhipeng, Huang, Ling, Huang, Wei·2018·Nature Communications
DOI 10.1038/s41467-018-05040-8PMC PMC6043560
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Abstract

Considerable achievements on multiple emission capabilities and tunable wavelengths have been obtained in inorganic luminescent materials. However, the development of organic counterparts remains a grand challenge. Herein we report a series of 2-/2,6-aryl substituted boron-dipyrromethene dyes with wide-range and multi-fluorescence emissions across red and near infrared in their aggregation states. Experimental data of X-ray diffraction, UV–vis absorption, and room temperature fluorescence spectra have proved the multiple excitation and easy-adjustable emission features in aggregated boron-dipyrromethene dyes. Temperature-dependent and time-resolved fluorescence studies have indicated a successive energy transfer from high to step-wisely lower-located energy levels that correspond to different excitation states of aggregates. Consistent quantum chemical calculation results have proposed possible aggregation modes of boron-dipyrromethene dyes to further support the above-described scenario. Thus, this study greatly enriches the fundamental recognition of conventional boron-dipyrromethene dyes by illustrating the relationships between multiple emission behaviors and the aggregation states of boron-dipyrromethene molecules.

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Crossref · 10.1038/s41467-018-05040-8

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Figures

Fig. 1 Structural details and fluorescent properties of BDP1. a Molecular structure of BDP1. b Molecular packing diagrams of BDP1 at room temperature extracted from single crystal XRD data. c Normalized photoluminescence (PL) spectra of BDP1 in solution (green curve) and microcrystalline powder state (red and gray curves)
Fig. 1 Structural details and fluorescent properties of BDP1. a Molecular structure of BDP1. b Molecular packing diagrams of BDP1 at room temperature extracted from single crystal XRD data. c Normalized photoluminescence (PL) spectra of BDP1 in solution (green curve) and microcrystalline powder state (red and gray curves)CC BY · PubMed Central
Fig. 2 Photophysical properties of BDP1 in THF and THF/water mixtures. a Absorption and emission spectra of BDP1 in THF at 1 × 10−5 mol L−1. b Absorption and c, d emission spectra of BDP1 in THF/water mixtures with varied volumetric fractions of water (fw)
Fig. 2 Photophysical properties of BDP1 in THF and THF/water mixtures. a Absorption and emission spectra of BDP1 in THF at 1 × 10−5 mol L−1. b Absorption and c, d emission spectra of BDP1 in THF/water mixtures with varied volumetric fractions of water (fw)CC BY · PubMed Central
Fig. 3 Fluorescent properties of aggregation-state BDP1. a Normalized fluorescence emission spectra of PMMA films prepared at different doping concentrations of BDP1. b, c Temperature-dependent emission spectra of microcrystalline powder state BDP1 collected from 97 to 497 K, excited at 480 nm. d Plots of normalized emission intensity changes of the multi-emissions at varying temperatures
Fig. 3 Fluorescent properties of aggregation-state BDP1. a Normalized fluorescence emission spectra of PMMA films prepared at different doping concentrations of BDP1. b, c Temperature-dependent emission spectra of microcrystalline powder state BDP1 collected from 97 to 497 K, excited at 480 nm. d Plots of normalized emission intensity changes of the multi-emissions at varying temperaturesCC BY · PubMed Central
Fig. 4 Time-resolved fluorescence properties of microcrystalline state BDP1. a Time-resolved fluorescence decay curves of BDP1 at emission wavelength (λem) of 500–800 nm. b Fluorescence decay curves of BDP1 at emission wavelengths of 605 and 768 nm. c Time-resolved emission spectra of BDP1 at the detection time from 0.35 to 5.45 ns d Time-resolved emission intensity variation of BDP1 at 605 and 768 nm. All samples measured were in microcrystalline powder state
Fig. 4 Time-resolved fluorescence properties of microcrystalline state BDP1. a Time-resolved fluorescence decay curves of BDP1 at emission wavelength (λem) of 500–800 nm. b Fluorescence decay curves of BDP1 at emission wavelengths of 605 and 768 nm. c Time-resolved emission spectra of BDP1 at the detection time from 0.35 to 5.45 ns d Time-resolved emission intensity variation of BDP1 at 605 and 768 nm. All samples measured were in microcrystalline powder stateCC BY · PubMed Central
Fig. 5 Theoretical calculations for mechanistic investigation. Calculated NTOs of BDP1 a dimer-1 and b trimer-1. c Schematic illustration of the proposed Domino-like energy transfer and subsequent multiple emissions in solid state BDP1
Fig. 5 Theoretical calculations for mechanistic investigation. Calculated NTOs of BDP1 a dimer-1 and b trimer-1. c Schematic illustration of the proposed Domino-like energy transfer and subsequent multiple emissions in solid state BDP1CC BY · PubMed Central
Fig. 6 Photophysical properties of microcrystalline state BDP2 to BDP6. Normalized fluorescence emissions (left column) of BDP2 to BDP6 in solution (green lines) and microcrystalline powder state (orange and red lines) with corresponding molecular structures in the right column
Fig. 6 Photophysical properties of microcrystalline state BDP2 to BDP6. Normalized fluorescence emissions (left column) of BDP2 to BDP6 in solution (green lines) and microcrystalline powder state (orange and red lines) with corresponding molecular structures in the right columnCC BY · PubMed Central

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Metadata

Authors
Tian, D., Qi, F., Ma, H., Wang, X., Pan, Y., Chen, R., Shen, Z., Liu, Z., Huang, L., & Huang, W.
Affiliations
  • Nanjing Tech University (CN)
  • Nanjing University of Posts and Telecommunications (CN)
  • Collaborative Innovation Center of Advanced Microstructures (CN)
Corresponding author
  • Shen, Zhen
  • Liu, Zhipeng
  • Huang, Ling
ORCID
Venue
Nature Communications
Publisher
Springer Science and Business Media LLC
Published
2018-07-12
Volume
9
Issue
1
Pages
2688-2688
ISSN
2041-1723 (ISSN-L)
DOI
10.1038/s41467-018-05040-8
PMC
PMC6043560
OpenAlex
W2854672850
Cited by
111
References
42
Citations by year
2026: 7 · 2025: 8 · 2024: 13 · 2023: 17 · 2022: 14 · 2021: 17 · 2020: 18 · 2019: 16 · 2018: 1
FWCI
4.85
Type
journal article
Language
en
Open access
Licence
Locations
  • Nature Communications (publishedVersion, cc-by)
  • Europe PMC (PubMed Central) (publishedVersion, other-oa)
  • PubMed Central (publishedVersion, cc-by)
  • PubMed (publishedVersion)
  • RePEc: Research Papers in Economics (submittedVersion)
  • DOAJ (DOAJ: Directory of Open Access Journals) (submittedVersion)
  • DOAJ (DOAJ: Directory of Open Access Journals) (submittedVersion, cc-by-sa)
Funders
National Natural Science Foundation of China (21371095)
Topics
  • Physical Sciences › Materials Science › Materials Chemistry › Luminescence and Fluorescent Materials
  • Physical Sciences › Chemistry › Spectroscopy › Molecular Sensors and Ion Detection
  • Physical Sciences › Chemistry › Physical and Theoretical Chemistry › Photochemistry and Electron Transfer Studies
Keywords
BODIPY dyes, boron dipyrromethene, red fluorescence, near-infrared emission, aggregation-induced emission, aggregation state, excitation states, quantum chemical calculations, aggregation modes

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