Facile ACQ-to-AIE transformation <i>via</i> diphenylphosphine (DPP) modification with versatile properties

Ma, Yuguo; Ye, Fangjun; Shen, Chengzhen; Guan, Jianxin; Liu, Yiming; Wang, Xiaoge; Wang, Jingtian; Cong, Ming; Wang, Weibin; Zhang, Ting; Zou, Bo; Zheng, Junrong

doi:10.1039/d1tc05810j

Cited by 10 publications

(8 citation statements)

References 75 publications

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“…As well, some investigations are highlighting the piezochromic luminescence of AIEgens in the near-infrared range and the AIE-to-ACQ transformation. [60][61][62][63][64][65][66][67][68] These investigations seem to establish a common rule that the piezochromic luminescence of AIEgens with raising pressure principally performs an initially enhanced emission tendency and then follows a gradually decayed tendency. It is assigned to the AIEgens with flexible molecular conformations.…”

Section: Introductionmentioning

confidence: 89%

The crucial role of planar π-conjugated segment in the molecular conformation of diphenyldibenzofulvene derivatives in crystals contributing to reducing emission energy

Fang

Wei

et al. 2022

Preprint

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Aggregation-induced emission luminogens (AIEgens) have been treated as one kind of the most important materials utilized in applications including organic light-emitting diodes, sensors, biological therapies, and so on, owing to the intense emission in aggregated states. However, the optical performance of AIEgens seems do not simply abide by the empirical principle that the expanded π-conjugated molecular conformations acquire the emission with lower energy. The unexpected photophysical properties of AIEgens make molecular conformation design more difficult. Herein, to unveil the crucial factors dominating the optical performance of AIEgens, a series of diphenyldibenzofulvene (DPDBF) derivatives in crystals are utilized. After systematically analyzing the impact factors including molecular conformation parameters and intermolecular coupling, and further discussing with the calculation results by Gaussian 16, the emission energy of DPDBF derivatives in crystals is assigned to the tight connection with the conformation of the planar π-conjugated segment, but not the conformation torsion of phenyl blades or the intermolecular coupling. Although the expanded π-conjugated molecular conformation of the mentioned DPDBF derivatives does decline the energy gap between HOMO to LUMO to some degree, the Stokes shift effect which is dominantly impacted by the conformation of planar π-conjugated moiety can realize to adjust the emission energy in a much more efficient way.

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Section: Introductionmentioning

confidence: 89%

The crucial role of planar π-conjugated segment in the molecular conformation of diphenyldibenzofulvene derivatives in crystals contributing to reducing emission energy

Fang

Wei

et al. 2022

Preprint

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“…The primary objective of these chemical alterations is to prevent undesirable p-p stacking, which can result in luminescence quenching. This aim can be accomplished through several strategies, 8,9 including introducing flexible chains or charged groups to suppress p-p stacking, [10][11][12] designing and synthesizing molecules with specific structures to introduce twisted conformations, 13,14 and encapsulating fluorescent molecules in hosts to minimize intermolecular interactions 15 to regulate the stacking patterns of molecules in the aggregated state. 16 Among them, the modification of the type or position of substitution is a commonly used approach for fabricating new AIEgens from ACQ molecules by alleviating the impact of p-p stacking.…”

Section: Introductionmentioning

confidence: 99%

ACQ to AIE transformation of quinoline derivatives: modulating substituent electronic effects to alter excited-state reorganization energy distribution

Wang,

Zhang,

Huang

et al. 2023

J. Mater. Chem. C

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“…14 A relatively simple strategy adopted for expanding the repertoire of solid-emissive compounds makes use of traditional ACQ fluorophores, which are modified with suitable substituents to minimize close packing. 15,16 The 4-methylene-1,4-dihydropyridine (DHP) scaffold has been utilized in the design of fluorophores, which include AIEactive/solid-emissive molecules. 17−25 This simple scaffold permits the fine-tuning of their photophysical properties through substituents on its periphery.…”

Section: ■ Introductionmentioning

confidence: 99%

“…The π–π interaction-driven self-assembly can be minimized if the fluorophores have a partially or completely twisted geometry, but the synthesis of such molecules is a challenging task . A relatively simple strategy adopted for expanding the repertoire of solid-emissive compounds makes use of traditional ACQ fluorophores, which are modified with suitable substituents to minimize close packing. , …”

Section: Introductionmentioning

confidence: 99%

Substituent-Controlled Photophysical Responses in Dihydropyridine Derivatives and Their Application in the Detection of Volatile Organic Contaminants

Kanneth,

Mathew,

Parameswaran

et al. 2023

J. Org. Chem.

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In the ever-expanding realm of organic fluorophores, structurally simple and synthetically straightforward molecules with unique photophysical properties have received special attention. Among these, 1,4-dihydropyridine (DHP) is an important scaffold that permits fine-tuning of their photophysical properties through substituents on the periphery. Herein, we describe a series of solid-emissive N-substituted 2,6-dimethyl-4-methylene-1,4-dihydropyridine derivatives appended with electron-withdrawing substituents (dicyanomethylene or 2-dicyanomethylene-3-cyano-2,5-dihydrofuran) at the C-4 position and alkyl or alkylaryl groups on the DHP nitrogen. Electronic and steric tuning exerted by these substituents resulted in interesting photophysical properties such as negative solvatochromism, solidstate, and aggregation-induced emission (AIE). Theoretical calculations were carried out to explain the solvatochromic properties. Insight into the AIE properties was obtained through variable-temperature nuclear magnetic resonance and viscosity- and temperature-dependent emission studies. The variations in molecular packing in the crystal lattice with changes in the N-substituents contributed to the tuning of solid state emission properties. Detection of aromatic volatile organic compounds (VOCs) was achieved using the aggregates of the DHP derivatives. Among the VOCs, p-xylene elicited a significant enhancement in emission, allowing its detection at submicromolar levels.

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Facile ACQ-to-AIE transformation via diphenylphosphine (DPP) modification with versatile properties

Abstract: Aggregation-induced emission (AIE) materials are attracting increasing research interests due to their broad application potential. The major design strategy for AIE luminogens (AIEgens) is incorporating molecular rotors, such as tetraphenylethylene...

Cited by 10 publications

References 75 publications

The crucial role of planar π-conjugated segment in the molecular conformation of diphenyldibenzofulvene derivatives in crystals contributing to reducing emission energy

The crucial role of planar π-conjugated segment in the molecular conformation of diphenyldibenzofulvene derivatives in crystals contributing to reducing emission energy

ACQ to AIE transformation of quinoline derivatives: modulating substituent electronic effects to alter excited-state reorganization energy distribution

Substituent-Controlled Photophysical Responses in Dihydropyridine Derivatives and Their Application in the Detection of Volatile Organic Contaminants

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