Protonation of the imino nitrogen deactivates the excited state of imidazolin-5-one in the solid state

Building molecular machine has long been a dream of scientists as it is expected to revolutionize many aspects of technology and medicine. Implementing the solid-state molecular motion is the prerequisite for a practical molecular machine. However, few works on solid-state molecular motion have been reported and it is almost impossible to “see” the motion even if it happens. Here the light-driven molecular motion in solid state is discovered in two non-conjugated molecules s-DPE and s-DPE-TM, resulting in the formation of excited-state though-space complex (ESTSC). Meanwhile, the newly formed ESTSC generates an abnormal visible emission which is termed as clusteroluminescence. Notably, the original packing structure can recover from ESTSC when the light source is removed. These processes have been confirmed by time-resolved spectroscopy and quantum mechanics calculation. This work provides a new strategy to manipulate and “see” solid-state molecular motion and gains new insights into the mechanistic picture of clusteroluminescence.

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The development of aryl-substituted 2-phenylimidazo[1,2-a]pyridines (PIP) with various colors of excited-state intramolecular proton transfer (ESIPT) luminescence in the solid state

Journal of Materials Chemistry C ◽

10.1039/c6tc00376a ◽

2016 ◽

Vol 4 (16) ◽

pp. 3599-3606 ◽

Cited By ~ 21

Author(s):

Toshiki Mutai ◽

Tatsuya Ohkawa ◽

Hideaki Shono ◽

Koji Araki

Keyword(s):

Excited State ◽

Solid State ◽

Proton Transfer ◽

Intramolecular Proton Transfer ◽

Aryl Group ◽

Red Emission ◽

Wide Range

The color of ESIPT luminescence of HPIP is tuned in a wide range by the introduction of aryl group(s), and thus a series of PIPs showing blue to red emission is realized.

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Substitution Effect on 2-(Oxazolinyl)-phenols: Emission Color-Tunable, Minimalistic Excited-State Intramolecular Proton Transfer (ESIPT)-based Luminophores

10.26434/chemrxiv.14291434.v1 ◽

2021 ◽

Author(s):

Dominik Göbel ◽

Pascal Rusch ◽

Daniel Duvinage ◽

Tim Stauch ◽

Nadja C. Bigall ◽

...

Keyword(s):

Optical Properties ◽

Excited State ◽

Solid State ◽

Substitution Effect ◽

Optical Characterization ◽

Intramolecular Proton Transfer ◽

Substitution Pattern ◽

Emission Color ◽

Color Tunable

The synthesis and optical characterization of novel single-benzene ESIPT-based fluorophores is described in solid state and in solution. Special attention is given towards the influence of their unique substitution pattern on their optical properties. Depending on this pattern, aggregation induced emission or aggregation caused quenching (ACQ) is observed in the solid state.

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Aggregation induced emission-excited state intramolecular proton transfer based “ off-on ” fluorescent sensor for Al 3+ ions in liquid and solid state

Sensors and Actuators B Chemical ◽

10.1016/j.snb.2018.02.078 ◽

2018 ◽

Vol 263 ◽

pp. 585-593 ◽

Cited By ~ 26

Author(s):

Gulshan Kumar ◽

Kamaldeep Paul ◽

Vijay Luxami

Keyword(s):

Excited State ◽

Solid State ◽

Proton Transfer ◽

Fluorescent Sensor ◽

Intramolecular Proton Transfer ◽

Aggregation Induced Emission

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In Search of Excited-State Proton Transfer in the Lumichrome Dimer in the Solid State: Theoretical and Experimental Approach

The Journal of Physical Chemistry A ◽

10.1021/jp060072y ◽

2006 ◽

Vol 110 (14) ◽

pp. 4638-4648 ◽

Cited By ~ 16

Author(s):

Ewa Sikorska ◽

Igor Khmelinskii ◽

Maciej Kubicki ◽

Wiesław Prukała ◽

Marcin Hoffmann ◽

...

Keyword(s):

Excited State ◽

Solid State ◽

Proton Transfer ◽

Experimental Approach ◽

Excited State Proton Transfer

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Nitrile-Substituted 2-(Oxazolinyl)-Phenols: Minimalistic Excited-State Intramolecular Proton Transfer (ESIPT)-Based Fluorophores

10.26434/chemrxiv.11786196.v1 ◽

2020 ◽

Author(s):

Dominik Göbel ◽

Daniel Duvinage ◽

Tim Stauch ◽

Boris Nachtsheim

Keyword(s):

Excited State ◽

Solid State ◽

Proton Transfer ◽

Density Functional ◽

Intramolecular Proton Transfer ◽

Crystal Structure Analysis ◽

Quantum Yields ◽

Functional Theory ◽

Emission Properties ◽

Emission Enhancement

Herein, we present minimalistic single-benzene, excited-state intramolecular proton transfer (ESIPT) based fluorophores as powerful solid state emitters. The very simple synthesis gave access to all four regioisomers of nitrile-substituted 2(oxazolinyl)phenols (MW = 216.1). In respect of their emission properties they can be divided into aggregation-induced emission enhancement (AIEE) luminophores (1-CN and 2-CN), dual state emission (DSE) emitters (3-CN) and aggregation-caused quenching (ACQ) fluorophores (4‐CN). Remarkably, with compound 1-CN we discovered a minimalistic ESIPT based fluorophore with extremely high quantum yield in the solid state ΦF = 87.3% at λem = 491 nm. Furthermore, quantum yields in solution were determined up to ΦF = 63.0%, combined with Stokes shifts up till 11.300 cm–1. Temperature dependent emission mapping, crystal structure analysis and time-dependent density functional theory (TDDFT) calculations gave deep insight into the origin of the emission properties.

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