Enhanced emission of a pyridine-based luminogen by hydrogen-bonding to organic and polymeric phenols

Chien, Wei-Lun; Yang, Chih-Min; Chen, Tai-Lin; Li, Shu-Ting; Hong, Jin‐Long

doi:10.1039/c3ra22217a

Cited by 19 publications

(15 citation statements)

References 44 publications

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“…These interesting CEE properties also exist in blend systems. For example, the AEE-active blends of bis( pyridinylvinyl)anthracene (An2Py) 23 and bisphenol A (BPA), with good miscibility due to the facile hydrogen bond (H bonded) interactions between pyridinyl rings of the An2Py and hydroxyl (OH) groups of BPA, show a strong emission due to the CEE properties. Wide-angle X-ray diffraction (WAXD) spectra indicate that the incorporation of BPA generates a new crystal, within which the effective rotational restriction on the An2Py molecules results in blends emitting with a higher intensity than pure An2Py itself.…”

Section: Introductionmentioning

confidence: 99%

Crystallization-promoted emission enhancement of poly(l-lactide) containing a fluorescent salicylideneazine center with aggregation-enhanced emission properties

et al. 2015

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Fluorescent 1,2-bis(2,4-dihydroxybenzylidene)hydrazine (CN 4 OH) with aggregation-enhanced emission (AEE) properties was used as the initiator to induce the ring-opening polymerization (ROP) of L-lactide, resulting in polymer CN-PLLA(n)s containing an AEE-active CN center. With both pairs of p-and o-hydroxyl (OH) groups, CN 4 OH initiates an ROP of L-lactide solely with the p-OH groups and the resulting CN-PLLA(n)s are highly-emissive due to the rotational restriction imposed by the remaining p-OHs of the central CN unit. A study on the solid emission of CN-PLLA(n)s reveals that crystallization of the neighbouring PLLA chains, instead of the fluorescent CN center itself, determines the AEE activity, e.g. the emission of crystalline CN-PLLA(n)s is much higher in emission intensity than amorphous CN-PLLA(n)s.As restricted molecular rotation is the main mechanism leading to AEE activity, effective rotational restriction imposed by crystalline polylactide chains is responsible for the high emission of crystalline CN-PLLA (n)s, in contrast to the weak emission of amorphous CN-PLLAs. The emission promotion of the fluorescent CN center by the neighbouring polylactide chains is designated as crystallization-promoted emission enhancement (CPEE) and is the focus of the study. IntroductionIn 2001, Tang's group 1,2 discovered that the propeller-shaped molecule of 1-methyl-1,2,3,4,5-pentaphenylsilole (MPPS) emits strongly in the aggregated solution and solid film states despite being non-emissive in a dilute solution. This concentration-dependent emission behaviour was designated as aggregation-induced emission (AIE). With beneficial emission efficiency in the solid film state, lots of organic and polymeric fluorophores with AIE or aggregation-enhanced emission (AEE) properties 3-8 have been prepared and characterized. Although an AIE process may mechanistically be associated with pathways like J-aggregate formation (JAF), 9 twisted intramolecular charge transfer (TICT), 10-12 and excited-state intramolecular proton transfer (ESIPT), 13 the intrinsic mechanism is actually due to the effective restriction on the intramolecular motions of the AIE-active fluorophores. A study 14 on the AIEactive fluorophores of different molecular shapes has concluded that restrictions of intramolecular rotations and vibrations (RIR and RIV) are the main causes for the AIE phenomenon observed in the propeller-shaped and shell-like fluorophores, respectively. Similar to the first discovered silole derivative of MPPS, 1,2 most of the AIE-active fluorophores are propeller-like molecules. In the aggregated state of MPPS, the sluggish molecular rotation 15,16 of aromatic rings reduces the possibilities of non-radiative decay pathways and results in an enhanced emission.Crystallization is an important factor contributing to the intense solid state emission in view of the fact that fluorophores with crystallization-enhanced emission (CEE) 17-22 properties are highly-emissive in the solid crystalline state but are weakly emissive when they are in the am...

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Section: Introductionmentioning

confidence: 99%

Crystallization-promoted emission enhancement of poly(l-lactide) containing a fluorescent salicylideneazine center with aggregation-enhanced emission properties

et al. 2015

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“…Indeed, pyridine is known to interact strongly with metal via the formation of a covalent bond through the lone pair of electrons of the nitrogen atom [39]. Moreover, this compound is very beneficial for the detection of phenols or catechols due to the formation of hydrogen bonds between the hydroxyl functions of bisphenols and the nitrogen atoms contained in pyridine [40]. In order to functionalize the AgNps surface, a solution of pyridine was added to the AgNps suspension just before the addition of the sample.…”

Section: Development Of the Sers Methodsmentioning

confidence: 99%

A simple approach for ultrasensitive detection of bisphenols by multiplexed surface-enhanced Raman scattering

Bleye

Dumont

Hubert

et al. 2015

Analytica Chimica Acta

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“…Severaln ew approaches involving different methods to afford rigid and twisted molecules with high luminescencei ns olution and in the solid state have been reported in the literature. [5][6][7][8][9][10] The introductiono f bulky substituents on the periphery,c onjugation-induced rigidity,l ocking of the aromatic rings with heteroatoms,h ydrogen bondinga nd metal ionc omplexation are some of the strategies used to afford molecules with high luminescence in the solid state and in solution. [5][6][7][8][9][10] Coordination-driven self-assembly is ap otential approach to assembled esired buildingb locks in as pecific pattern to obtainm olecular architectures with desirable properties.…”

Section: Introductionmentioning

confidence: 99%

Aggregation‐Induced Emission of Platinum(II) Metallacycles and Their Ability to Detect Nitroaromatics

Chowdhury

Howlader

Mukherjee

2016

Chemistry A European J

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Two new acceptors containing platinum-carbazole (1) and platinum-triphenylamine (2) backbones with bite angles of 90° and 120°, respectively, have been synthesised and characterised. Reactions of the rigid acceptor 1 with linear dipyridyl-based donors (3 and 4) generated [4+4] self-assembled molecular squares (5 and 6), and similar treatments with acceptor 2 instead of 1 yielded [6+6] self-assembled molecular hexagons (7 and 8). The metallacycles were characterised by multinuclear NMR spectroscopy ((1) H and (31) P) and ESI-MS. The geometries of the metallacycles were optimised by using the PM6 method. When aggregates of the metallacycles were formed by adding hexane solutions in dichloromethane, aggregation-induced emission was observed for metallacycles 5 and 7, and aggregation-caused quenching was observed for metallacycles 6 and 8. The formation of aggregates was verified by dynamic light scattering and TEM analyses. Macrocycles 5 and 7 are white-light emitters in THF. Moreover, their high luminescence in both solution and the solid state was utilised for the recognition of nitroaromatic explosives.

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Enhanced emission of a pyridine-based luminogen by hydrogen-bonding to organic and polymeric phenols

Cited by 19 publications

References 44 publications

Crystallization-promoted emission enhancement of poly(l-lactide) containing a fluorescent salicylideneazine center with aggregation-enhanced emission properties

Crystallization-promoted emission enhancement of poly(l-lactide) containing a fluorescent salicylideneazine center with aggregation-enhanced emission properties

A simple approach for ultrasensitive detection of bisphenols by multiplexed surface-enhanced Raman scattering

Aggregation‐Induced Emission of Platinum(II) Metallacycles and Their Ability to Detect Nitroaromatics

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