Control of crystal structures of fluorescent two-component supramolecular systems by varying substituents and their positions

Tanaka, Yūki; Tabata, Hideyuki; Tajima, Nobuo; Kuroda, Reiko; Imai, Yoshitane

doi:10.1039/c3ce42128g

Cited by 4 publications

(3 citation statements)

References 23 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Several compounds that are fluorescent in solution are non‐fluorescent in solid‐state . Emission properties of certain organic compounds in solid state change upon formation of cocrystals behave as fluorescent and phosphorescent material. It is a well known fact that molecular orientations and stacking arrangements among fluorophores in crystal structure tunes luminescence properties of organic materials .…”

Section: Introductionmentioning

confidence: 99%

Resonance Energy Transfer Emission Observed in Cocrystal of N,N′-Bis(3-imidazol-1-ylpropyl)naphthalenediimide with Cinnamic Acid

Tarai

Baruah

2017

ChemistrySelect

View full text Add to dashboard Cite

Cocrystal of N,N′‐bis(3‐imidazol‐1‐ylpropyl)naphthalenediimide with 3‐hydroxybenzoic acid has parallel stacks among naphthalenediimide rings (A) as ‐A−A‐A−A‐ like arrangement; whereas in packing of 5‐aminoisophthalate (D) salt of N,N′‐bis(3‐imidazol‐1‐ylpropyl) naphthalenediimide has stack of parallel aromatic rings in a manner like ‐A−D‐A−D‐. Parallel stacking patterns among the fluorescent aromatic rings of these adducts influence fluorescence. Fluorescence of solid sample of cocrystal with 3‐hydroxybenzoic acid or salt with 5‐aminoisophthalic acid of N,N′‐bis(3‐imidazol‐1‐ylpropyl)naphthalenediimide is quenched due to Dexter electron transfer. Cocrystal of N,N′‐bis(3‐imidazol‐1‐ylpropyl)naphthalenediimide with cinnamic acid is devoid of parallel stacks among fluorophoric aromatic rings. It shows emission at 547 nm through resonance energy transfer between donor and acceptor components. The original parent components have individual fluorescence emissions at comparable wavelengths but much shorter wavelengths than the wavelength of emission shown by the cocrystal.

show abstract

Section: Introductionmentioning

confidence: 99%

Resonance Energy Transfer Emission Observed in Cocrystal of N,N′-Bis(3-imidazol-1-ylpropyl)naphthalenediimide with Cinnamic Acid

Tarai

Baruah

2017

ChemistrySelect

View full text Add to dashboard Cite

show abstract

“…So far, the most effective interactions are the hydrogen bond (HB) 18,19 and the halogen bond (XB). 20,21 The use of co-crystals as a means to modify optical properties such as fluorescence 16,[22][23][24][25][26][27] and phosphorescence 28-33 of luminescent molecules is a strategy showing very promising results, whereas the systematic investigation of photophysical parameters, such as emission quantum yields and lifetimes, is still a less explored path. This study deals with a series of isomers containing a 4-piperidinyl-1,8-naphthalimide as the photoactive core, and at the N-position one of three different n-methylpyridines (n = 2, 3 or 4; see Scheme 1).…”

Section: Introductionmentioning

confidence: 99%

“…So far, the most effective interactions are the hydrogen bond (HB) 18,19 and the halogen bond (XB). 20,21 The use of co-crystals as a means to modify optical properties such as fluorescence 16,[22][23][24][25][26][27] and phosphorescence [28][29][30][31][32][33] of luminescent molecules is a strategy showing very promising results, whereas the systematic investigation of photophysical parameters, such as emission quantum yields and lifetimes, is still a less explored path.…”

Section: Introductionmentioning

confidence: 99%

Fluorescent crystals and co-crystals of 1,8-naphthalimide derivatives: synthesis, structure determination and photophysical characterization

et al. 2015

View full text Add to dashboard Cite

A series of 4-pyperidinyl-1,8-naphtalimide derivatives containing at the N-position an n-methylpyridine (n = 2, 3, or 4) have been synthesized and isolated as crystalline materials. These isomers were further reacted, in the solid state, with the coformer 1,4-diiodotetrafluorobenzene (I2F4) to give three new co-crystals of general formula n2•I2F4. All crystalline materials have been thoroughly characterized in the solid state via single-crystal and powder X-ray diffraction, infrared spectroscopy and thermal methods; in addition, the photophysical properties of all compounds have been investigated in solution and in the solid state. The fluorescence features of the crystalline solids depend on the different arrangement of the molecules in the lattice and co-crystallization leads to important changes in the emission properties of the crystalline compounds. Emission quantum yields of the solids vary between 0.11 and 0.50. ‡ Results and discussion Synthesis and crystal growthThe synthetic strategy employed for isomers 2-4 is based on two high yielding steps, namely (i) direct reaction between the 4-bromo-1,8-naphthalic anhydride and piperidine in the high boiling solvent 2-methoxyethanol, as reported in the literature, 46, 47 followed by (ii) condensation with 2, 3 or 4-picolylamine in a mixture of water and ethanol in basic ambient (Scheme 1). Graphical AbstractFluorescent crystals were obtained by solid-state co-crystallization of 4-pyperidinyl-1,8-naphtalimide derivatives with a halogenated co-former.

show abstract

Effects of strong hydrogen bonds and weak intermolecular interactions on supramolecular assemblies of 4-fluorobenzylamine

Wang

Ding

et al. 2015

Journal of Molecular Structure

View full text Add to dashboard Cite

Control of crystal structures of fluorescent two-component supramolecular systems by varying substituents and their positions

Cited by 4 publications

References 23 publications

Resonance Energy Transfer Emission Observed in Cocrystal of N,N′-Bis(3-imidazol-1-ylpropyl)naphthalenediimide with Cinnamic Acid

Resonance Energy Transfer Emission Observed in Cocrystal of N,N′-Bis(3-imidazol-1-ylpropyl)naphthalenediimide with Cinnamic Acid

Fluorescent crystals and co-crystals of 1,8-naphthalimide derivatives: synthesis, structure determination and photophysical characterization

Effects of strong hydrogen bonds and weak intermolecular interactions on supramolecular assemblies of 4-fluorobenzylamine

Contact Info

Product

Resources

About