Abstract
Tuning and controlling the solid-state photophysical properties of organic luminophore are very important to develop next-generation organic luminescent materials. With the aim of discovering new functional luminescent materials, new cocrystals of 9-anthracene carboxylic acid (ACA) were prepared with two different dipyridine coformers: 1,2-bis(4-pyridyl)ethylene and 1,2-bis(4-pyridyl)ethane. The cocrystals were successfully obtained by both mechanochemical approaches and conventional solvent crystallization. The newly obtained crystalline solids were characterized thoroughly using a combination of single crystal X-ray diffraction, powder X-ray diffraction, Fourier-transform infrared spectroscopy, differential thermal analysis, and thermogravimetric analysis. Structural analysis revealed that the cocrystals are isostructural, exhibiting two-fold interpenetrated hydrogen bonded networks. While the O–H···N hydrogen bonds adopts a primary role in the stabilization of the cocrystal phases, the C–H···O hydrogen bonding interactions appear to play a significant role in guiding the three-dimensional assembly. Both π···π and C–H···π interactions assist in stabilizing the interpenetrated structure. The photoluminescence properties of both the starting materials and cocrystals were examined in their solid states. All the cocrystals display tunable photophysical properties as compared to pure ACA. Density functional theory simulations suggest that the modified optical properties result from charge transfers between the ACA and coformer molecules in each case. This study demonstrates the potential of crystal engineering to design solid-state luminescence switching materials through cocrystallization.
Highlights
IntroductionOrganic solid-state luminescent materials have been studied widely over the last decade [1,2,3]
Organic solid-state luminescent materials have been studied widely over the last decade [1,2,3].This attention owes to their appealing and versatile optoelectronic applications in the fields of laser technology [4], chemical/biological sensors [5], and for organic light-emitting diodes [6]
Hydrogen bonding interaction energies were calculated within the framework of the symmetry adapted perturbation theory (SAPT), as implemented in PSI4 [52]
Summary
Organic solid-state luminescent materials have been studied widely over the last decade [1,2,3]. New approaches are needed to switch and tune the emission wavelength of organic chromophores to meet the needs of next-generation light-emitting materials In this context, cocrystallization has become a popular tool. The authors ascribed the improved efficiency to the effective energy transfer In other cases, such as in cocrystals of 2,6-biphenyl-4-pyrone with different carboxylic acids, the luminescent properties of the luminophore could be completely altered [22]. The applied dipyridine linkers here are widely employed for the design of molecular materials, as well as functional coordination complexes [33,34] and coordination framework compounds [35,36,37,38] Both multicomponent solids were characterized by experimental methods.
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