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Solid-State Emission Enhancement via Molecular Engineering of Benzofuran Derivatives.

ABSTRACT: A series of linear benzofuran derivatives consisting of either a vinylene or a cyanovinylene were prepared in order to investigate their emission properties. The X-ray crystallography of structurally similar derivatives was also evaluated. The crystalline structures of the vinylene derivatives showed only lateral contacts that involved the benzofurans and no ?-stacking. In contrast, ?-stacking was observed for the bisbenzofuran and benzofuran-phenyl cyanovinylene derivatives. No intermolecular ?-? stacking was observed for the extended cyanovinylene structures. Intermolecular bonding between the nitrile and a furan atom was found. The fluorescence quantum yields (?_fl) of the vinylene derivatives were consistently high (>50%) in both solution and the crystal state. The exception was the benzofuran-furan-vinylene-phenyl, the ?_fl of which was <10% when in the solid state. The cyanovinylene counterparts emitted weakly in solution (?_fl < 2%). Their luminogenic property was demonstrated with a ca. 15-fold increase in emission in the solid state. A 6-fold emission enhancement was also found when they were aggregated in a 90 vol% methanol/water mixture. The solid-state emission enhancement of the cyanovinylene benzofurans was in part attributable to intermolecular contacts that suppressed excited-state deactivation by molecular motion.

SUBMITTER: Grolleau J

PROVIDER: S-EPMC6643477 | biostudies-literature | 2018 Dec

REPOSITORIES: biostudies-literature

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Solid-State Emission Enhancement via Molecular Engineering of Benzofuran Derivatives.

Grolleau Jérémie J Petrov Ravil R Allain Magali M Skene William G WG Frère Pierre P

ACS omega 20181227 12

A series of linear benzofuran derivatives consisting of either a vinylene or a cyanovinylene were prepared in order to investigate their emission properties. The X-ray crystallography of structurally similar derivatives was also evaluated. The crystalline structures of the vinylene derivatives showed only lateral contacts that involved the benzofurans and no π-stacking. In contrast, π-stacking was observed for the bisbenzofuran and benzofuran-phenyl cyanovinylene derivatives. No intermolecular π ...[more]

PMID: 31458425

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Project description:In this work, a series of γ-substituted diphenylnaphthalonitriles were synthesized and characterized. They show efficient emission in solution and in the aggregated state and their environment responsiveness is based on having variable substituents at the para-position of the two phenyl moieties. The excited state properties were fully investigated in tetrahydrofuran (THF) solutions and in THF/H2O mixtures. The size of the aggregates in aqueous media were measured by dynamic light scattering (DLS). The steady-state and time-resolved photoluminescence spectroscopy studies revealed that all the molecules show intense fluorescence both in solution and in the aggregated state. In THF solutions, a blue emission was observed for the unsubstituted (H), methyl- (Me) and tert-butyl- (t-Bu) substituted γ-diphenylnaphthalonitriles, which can be attributed to a weak π-donor capability of these groups. On the other hand, the methoxy- (OMe), methylsulfanyl- (SMe) and dimethylamino- (NMe2) substituted compounds exhibit a progressive red-shift in emission compared to H, Me and t-Bu due to a growing π-electron donating capability. Interestingly, upon aggregation in water-containing media, H, Me and t-Bu show a slight red-shift of the emission and a blue-shift is observed for OMe, SMe and NMe2. The crystal structure of Me allowed a detailed discussion of the structure-property relationship. Clearly, N-containing substituents such as NMe2 possess more electron-donating ability than the S-based moieties such as SMe. Moreover, it was found that NMe2 showed higher luminescence quantum yields (ΦF) in comparison to SMe, indicating that N-substituted groups could enhance the fluorescence intensity. Therefore, the π-donor nature of the substituents on the phenyl ring constitutes the main parameter that influences the photophysical properties, such as excited state lifetimes and photoluminescence quantum yields. Hence, a series of highly luminescent materials from deep blue to red emission depending on substitution and environment is reported with potential applications in sensing, bioimaging and optoelectronics.

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Solid-State Emission Enhancement via Molecular Engineering of Benzofuran Derivatives.

Publications

Solid-State Emission Enhancement via Molecular Engineering of Benzofuran Derivatives.

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