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Alkyl- π engineering in state control toward versatile optoelectronic soft materials

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ABSTRACT

Organic π-conjugated molecules with extremely rich and tailorable electronic and optical properties are frequently utilized for the fabrication of optoelectronic devices. To achieve high solubility for facile solution processing and desirable softness for flexible device fabrication, the rigid π units were in most cases attached by alkyl chains through chemical modification. Considerable numbers of alkylated-π molecular systems with versatile applications have been reported. However, a profound understanding of the molecular state control through proper alkyl chain substitution is still highly demanded because effective applications of these molecules are closely related to their physical states. To explore the underlying rule, we review a large number of alkylated-π molecules with emphasis on the interplay of van der Waals interactions (vdW) of the alkyl chains and π–π interactions of the π moieties. Based on our comprehensive investigations of the two interactions’ impacts on the physical states of the molecules, a clear guidance for state control by alkyl-π engineering is proposed. Specifically, either with proper alkyl chain substitution or favorable additives, the vdW and π–π interactions can be adjusted, resulting in modulation of the physical states and optoelectronic properties of the molecules. We believe the strategy summarized here will significantly benefit the alkyl-π chemistry toward wide-spread applications in optoelectronic devices.

No MeSH data available.


(a) Chemical structures of an anthracene derivative 27 and a Pt(II) porphyrin photosensitizer St. (b) Photograph of the doped liquid (St/27 = 0.01 mol%) exposed to a 532 nm laser. Reprinted with permission from P Duan et al 2013 J. Am. Chem. Soc.135 19056, © 2013 American Chemical Society .
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Figure 20: (a) Chemical structures of an anthracene derivative 27 and a Pt(II) porphyrin photosensitizer St. (b) Photograph of the doped liquid (St/27 = 0.01 mol%) exposed to a 532 nm laser. Reprinted with permission from P Duan et al 2013 J. Am. Chem. Soc.135 19056, © 2013 American Chemical Society .

Mentions: Inspired by our research on photostable liquid luminophors, the Kimizuka group synthesized an anthracene liquid, 27 (figure 20(a)), and applied it to an upconversion (UC) luminescent system [92]. Liquid 27 can accommodate a Pt(II) porphyrin photosensitizer, St, resulting in UC properties upon light irradiation with a 532 nm green laser (figure 20(b)). Compared with a traditional UC system, which was functionalized in an organic solvent and suffered emission quenching by molecular oxygen, this new UC system exhibited strong emission features, with a high quantum yield of 28% free from the oxygen effect due to the oxygen-impermeable solvent-free liquid system.


Alkyl- π engineering in state control toward versatile optoelectronic soft materials
(a) Chemical structures of an anthracene derivative 27 and a Pt(II) porphyrin photosensitizer St. (b) Photograph of the doped liquid (St/27 = 0.01 mol%) exposed to a 532 nm laser. Reprinted with permission from P Duan et al 2013 J. Am. Chem. Soc.135 19056, © 2013 American Chemical Society .
© Copyright Policy - open-access
Related In: Results  -  Collection

License 1 - License 2
Show All Figures
getmorefigures.php?uid=PMC5036497&req=5

Figure 20: (a) Chemical structures of an anthracene derivative 27 and a Pt(II) porphyrin photosensitizer St. (b) Photograph of the doped liquid (St/27 = 0.01 mol%) exposed to a 532 nm laser. Reprinted with permission from P Duan et al 2013 J. Am. Chem. Soc.135 19056, © 2013 American Chemical Society .
Mentions: Inspired by our research on photostable liquid luminophors, the Kimizuka group synthesized an anthracene liquid, 27 (figure 20(a)), and applied it to an upconversion (UC) luminescent system [92]. Liquid 27 can accommodate a Pt(II) porphyrin photosensitizer, St, resulting in UC properties upon light irradiation with a 532 nm green laser (figure 20(b)). Compared with a traditional UC system, which was functionalized in an organic solvent and suffered emission quenching by molecular oxygen, this new UC system exhibited strong emission features, with a high quantum yield of 28% free from the oxygen effect due to the oxygen-impermeable solvent-free liquid system.

View Article: PubMed Central - PubMed

ABSTRACT

Organic π-conjugated molecules with extremely rich and tailorable electronic and optical properties are frequently utilized for the fabrication of optoelectronic devices. To achieve high solubility for facile solution processing and desirable softness for flexible device fabrication, the rigid π units were in most cases attached by alkyl chains through chemical modification. Considerable numbers of alkylated-π molecular systems with versatile applications have been reported. However, a profound understanding of the molecular state control through proper alkyl chain substitution is still highly demanded because effective applications of these molecules are closely related to their physical states. To explore the underlying rule, we review a large number of alkylated-π molecules with emphasis on the interplay of van der Waals interactions (vdW) of the alkyl chains and π–π interactions of the π moieties. Based on our comprehensive investigations of the two interactions’ impacts on the physical states of the molecules, a clear guidance for state control by alkyl-π engineering is proposed. Specifically, either with proper alkyl chain substitution or favorable additives, the vdW and π–π interactions can be adjusted, resulting in modulation of the physical states and optoelectronic properties of the molecules. We believe the strategy summarized here will significantly benefit the alkyl-π chemistry toward wide-spread applications in optoelectronic devices.

No MeSH data available.