Regulation of π-stacked anthracene arrangement for fluorescence modulation of organic solid from monomer to excited oligomer emission.

  title={Regulation of $\pi$-stacked anthracene arrangement for fluorescence modulation of organic solid from monomer to excited oligomer emission.},
  author={Tomoaki Hinoue and Yuta Shigenoi and Misa Sugino and Yuji Mizobe and Ichiro Hisaki and Mikiji Miyata and Norimitsu Tohnai},
  volume={18 15},
The construction and precise control of the face-to-face π-stacked arrangements of anthracene fluorophores in the crystalline state led to a remarkable red shift in the fluorescence spectrum due to unprecedented excited oligomer formation. The arrangements were regulated by using organic salts including anthracene-1,5-disulfonic acid (1,5-ADS) and a variety of aliphatic amines. Because of the smaller number of hydrogen atoms at the edge positions and the steric effect of the sulfonate groups, 1… Expand
Discrete face-to-face stacking of anthracene inducing high-efficiency excimer fluorescence in solids via a thermally activated phase transition
It is always a challenge for planar polycyclic aromatic molecules to achieve high efficiency in solids owing to their frequent encounter with aggregation-caused quenching (ACQ). An anthraceneExpand
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1-Acetyl-3-(4-methoxyphenyl)-5-(1-pyrenyl)-pyrazoline (AMPP) was synthesized and crystallized to yield three types of crystals with different host–guest structures: AMPP crystal (I), AMPP–phenol (II)Expand
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1-Acetyl-3-phenyl-5-(1-pyrenyl)-pyrazoline (APPP) was synthesized and formed four types of different crystals under different crystallization conditions: guest-free crystal (I, α polymorph),Expand
Discrete Dimeric Anthracene Stackings in Solids with Enhanced Excimer Fluorescence
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Investigation of molecular arrangements and solid-state fluorescence properties of solvates and cocrystals of 1-acetyl-3-phenyl-5-(9-anthryl)-2-pyrazoline
The title compound (APAP) was crystallized under different conditions to afford five types of crystals: the guest-free crystal (I), APAP·chloroform solvate (II), the APAP·phenol cocrystal (III), theExpand
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Abstract With “saddle” shaped tetra[3,4-Thienylene] (TT) as a rigid 3D spacer, three anthryl substituted TT compounds, 1-(anthracen-9-yl)[3,3′-bithiophene] (TTA-1),Expand
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A unique cyano substituted styrene pyridinium with interesting solid-state fluorescence that can be finely tuned by simple change of counteranions is described, which endows the crystal of PyNO3 with anisotropic fluorescence. Expand
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The results suggest that simply linking the m-carborane fragment to one anthracenes unit through a CH2 spacer produces a significant enhancement of the fluorescence in the final fluorophore, probably due to the free rotation of the anthracene linked to the Ccluster. Expand
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The prospect of tuning the energy of emitting states through external stimuli opens the possibility of shifting the energy of emitting units on demand and controlling the bimolecular processes theyExpand
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A series of 2,2-disubstituted benzothiazoline-BMes2 (Mes = mesityl) compounds containing a B═N bond have been prepared and fully characterized. Their photophysical properties were investigated byExpand


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Crystal packing structures of 9,10-dimethoxyanthracene (1), 9,10-bis(methylthio)anthracene (2), and 9,10-bis(methyltelluro)anthracene (3) were revealed by X-ray crystallographic analysis as modelsExpand
Systematic investigation of molecular arrangements and solid-state fluorescence properties on salts of anthracene-2,6-disulfonic acid with aliphatic primary amines.
Systematic investigation of the organic salts of anthracene-2,6-disulfonic acid with a wide variety of primary amines constructs a library of arrangements and properties, and the library leads to remarkable strategies for the development of organic solid materials. Expand
Molecular Packing and Solid-State Fluorescence of Alkoxy-Cyano Substituted Diphenylbutadienes: Structure of the Luminescent Aggregates
A detailed study on the photophysical properties of a series of alkoxy substituted diphenylbutadienes in solution and in the solid state providing a molecular level understanding of the factorsExpand
A highly fluorescent anthracene-containing hybrid material exhibiting tunable blue-green emission based on the formation of an unusual "T-shaped" excimer.
1H NMR spectroscopic studies in nonaqueous or aqueous solution confirmed this T-shaped conformation of anthracene, which is consistent with the results of single-crystal X-ray structure analysis and solid-state photoluminescence studies. Expand
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The main purpose of this study is to grow an organic thin film consisting of aromatic molecules with enhanced π-conjugations. For this purpose, an anthracene derivative, 9,10-bis (methylthio)Expand
The influence of side chains on the structures and properties of functionalized pentacenes
We investigated substituent-induced variations in microstructure and physical properties of a family of functionalized pentacenes, materials currently of intensive interest for making organicExpand
Phase-Dependent Emission of Naphthalene−Anthracene-Based Concave-Shaped Molecules
Fluorescence spectra of aromatic chain imides possessing anthracene and naphthalene moieties were examined both in solution and in the solid state. Depending on the substituents at the imide nitrogenExpand
Electronic and optical properties in the solid-state molecular assemblies of anion-responsive pyrrole-based π-conjugated systems.
By anion complexation, inclusion of the counter cations into the crystals has been found to be one of the essential factors to determine the properties of dipyrrolyldiketone boron complexes as π-conjugated acyclic anion receptors. Expand
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The study reports the solid state photophysical properties of a series of alkyloxy-substituted oligo(phenyleneethynylene)s, methoxy to hexyloxy, supported by a detailed analysis of molecular packingExpand
Bis(methylthio)tetracenes: synthesis, crystal-packing structures, and OFET properties.
X-ray crystallographic data revealed that 2 is arranged as a result of a 1-D slipped-cofacial π-stacking with S-S and S-π interactions, similar to the packing arrangement of 6,13-bis(methylthio)pentacene (1), whereas 3 exhibits a herringbone packing arrangement without S- S interactions. Expand