Polymorph crystal packing effects on charge transfer emission in the solid state

He, Xiaoyan; Benniston, Andrew C.; Saarenpää, Hanna; Lemmetyinen, Helge; Tkachenko, Nikolia V.; Baisch, Ulrich

doi:10.1039/c5sc01151e

Cited by 30 publications

(22 citation statements)

References 43 publications

(16 reference statements)

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Ease of synthesis, photostability, color purity, and high luminescence quantum efficiency are the essential factors for the development of new luminescent compounds. Solid‐state emissive properties of organic chromophores depend on their structure, crystal packing, and intermolecular and intramolecular interactions . Different intermolecular interactions such as π–π stacking, hydrogen bonding (C−H⋅⋅⋅O, C−H⋅⋅⋅π, C−H⋅⋅⋅N, O−H⋅⋅⋅N), and noncovalent forces determine the fluorescence quantum efficiency of chromophores in the solid state .…”

Section: Introductionmentioning

confidence: 99%

π–π Interactions: Influence on Molecular Packing and Solid‐State Emission of ESIPT and non‐ESIPT Motifs

et al. 2016

View full text Add to dashboard Cite

Novel, triphenylamino benzothiazole-based excited-state intramolecular protont ransfer (ESIPT) and non-ESIPT fluorophores were prepared by Suzuki coupling reactions. Their photophysical properties in solution,a queous suspension,a nd in the solids tate were systematically investigated. High fluorescenceq uantum efficiencies (F sol % 95 %; F solid % 88 %), moderate Stokes shifts ( % 8000 cm À1 ), microenvironment-sensitive and molecular-framework-dependent emission are the striking features of the protocol described here. Solid-state emission was modulated and interpreteda s ac rossover effect of p-p interactions using single-crystal Xray analyses. The nonplanar/twisted framework of the system helps to avoid noncovalenti nteractions, facilitating the suppression of fluorescenceq uenching in the solid state with high quantum efficiency over 88 %.[a] Dr.Supporting information and the ORCID identification number(s) for the author(s) of this article can be found under http://dx.

show abstract

Section: Introductionmentioning

confidence: 99%

π–π Interactions: Influence on Molecular Packing and Solid‐State Emission of ESIPT and non‐ESIPT Motifs

et al. 2016

View full text Add to dashboard Cite

show abstract

“…In contrast the notorious aggregation-caused quenching (ACQ), branchy and twisted aggregation-induced emission (AIE) and aggregation-induced emission enhancement (AIEE) fluorogens are developed to tune the intermolecular stacking for efficient emissions in the solid state29303132. Alternative ways to regulate multifunctional materials are allomorphism and mischcrystal333435. This strategy do not involves tedious organic synthesis.…”

mentioning

confidence: 99%

Anion-controlled dimer distance induced unique solid-state fluorescence of cyano substituted styrene pyridinium

Zhang

Kong

et al. 2016

Sci Rep

View full text Add to dashboard Cite

Molecular packing arrangements play a key role in dominating the photophysical properties of luminophores in aggregated state but fine control of the molecular packing is a great challenge. This article describes a unique cyano substituted styrene pyridinium with interesting solid-state fluorescence that can be finely tuned by simple change of counteranions. The dilute solutions of the organic salts (PyCl, PyNO3, PyOTs and PyPh4B) exhibit very weak fluorescence. The crystals of the organic salts (PyCl, PyNO3, and PyOTs) show much enhanced fluorescence compared with their dilute solutions. It is interesting that the emissions changed from bluish-green to deep-blue and fluorescence quantum yields increase from 2.5% to 13.1% with the increasing of steric hindrance of the anions from chloridion, nitrate, to p-toluenesulfonate. Crystal and DFT studies reveal that the enhanced fluorescence is ascribed to the formation of dimers and bigger anions induce larger molecular separation in dimers. Tetraphenylboron anion with very large steric hindrance impedes the formation of dimers and thus results in non-fluorescent salt (PyPh4B). Meanwhile, this unique dimeric packing endows the crystal of PyNO3 with anisotropic fluorescence.

show abstract

“…The conclusion, therefore, is that MBIC emits charge‐recombination fluorescence in the crystalline phase. Although not unique, this behaviour is uncommon and attests to the fact that MBIC does not undergo substantial self‐quenching in the solid matrix. A temperature dependence emission study carried out with a single crystal of MBIC indicates that the re‐organization energy associated with charge‐recombination is approximately 1,530 cm −1 and the Huang–Rhys factor is 0.50.…”

Section: Resultsmentioning

confidence: 99%

Exciton Migration and Surface Trapping for a Photonic Crystal Displaying Charge‐Recombination Fluorescence

Al-Aqar

Atahan

Benniston

et al. 2016

Chemistry A European J

Self Cite

View full text Add to dashboard Cite

A compact donor-acceptor molecular dyad has been synthesized by attaching an N,N-dimethylamino fragment to a naphthalic anhydride residue. The dyad shows fluorescence from an intramolecular charge-transfer state (i.e., charge-recombination fluorescence) in solution, with the photo-physical properties being strongly dependent on the solvent polarity. Similar emission is seen for single crystals of the target compound, the molecules being aligned head-to-head, although time-resolved emission profiles display dual-exponential kinetics. A second polymorph with the head-to-tail alignment also gives rise to two lifetimes that differ somewhat from those of the first structure, which are assigned to bulk and surface-bound molecules. Growing the crystal in the presence of Rhodamine B localizes the dye around the surface. Excitation of the crystal is followed by sub-ps exciton migration along the aligned stacks, with occasional crossing to adjacent stacks and trapping at the surface. Rhodamine B present at very low levels acts as the acceptor for excitons entering the surface layer. Crystals embedded in a polyester resin form an artificial light-harvesting antenna able to sensitize an amorphous silicon solar cell.

show abstract

Polymorph crystal packing effects on charge transfer emission in the solid state

Abstract: Condensation of 1,8-naphthalic anhydride with N,N-(dimethylamino)aniline produced the donor-acceptor compound DMIM, which crystallised from a chloroform–diethyl ether mixture to afford two different coloured crystal polymorphs.

Cited by 30 publications

References 43 publications

π–π Interactions: Influence on Molecular Packing and Solid‐State Emission of ESIPT and non‐ESIPT Motifs

π–π Interactions: Influence on Molecular Packing and Solid‐State Emission of ESIPT and non‐ESIPT Motifs

Anion-controlled dimer distance induced unique solid-state fluorescence of cyano substituted styrene pyridinium

Exciton Migration and Surface Trapping for a Photonic Crystal Displaying Charge‐Recombination Fluorescence

Contact Info

Product

Resources

About