Fine‐Tuning Dual Emission and Aggregation‐Induced Emission Switching in NPI–BODIPY Dyads

Mukherjee, Sanjoy; Thilagar, Pakkirisamy

doi:10.1002/chem.201305049

Cited by 87 publications

(51 citation statements)

References 129 publications

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“…Their additional advantage is the ease of functionalization. Owing to the above properties, difluoroboranes have been used as optical switches [26][27][28][29][30][31], fluorescent probes [32][33][34][35][36][37][38], photosensitizers used in photochemotherapy [39][40][41][42][43][44][45], biomarkers [46][47][48][49][50], and TADF (Thermally-Activated Delayed Fluorescence) materials used for emitters for organic light-emitting diodes [51][52][53][54], among others.…”

Section: Introductionmentioning

confidence: 99%

Benchmarking Density Functional Approximations for Excited-State Properties of Fluorescent Dyes

Grabarz

Ośmiałowski

2021

Molecules

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This study presents an extensive analysis of the predictive power of time-dependent density functional theory in determining the excited-state properties of two groups of important fluorescent dyes, difluoroboranes and hydroxyphenylimidazo[1,2-a]pyridine derivatives. To ensure statistically meaningful results, the data set is comprised of 85 molecules manifesting diverse photophysical properties. The vertical excitation energies and dipole moments (in the electronic ground and excited states) of the aforementioned dyes were determined using the RI-CC2 method (reference) and with 18 density functional approximations (DFA). The set encompasses DFAs with varying amounts of exact exchange energy (EEX): from 0% (e.g., SVWN, BLYP), through a medium (e.g., TPSSh, B3LYP), up to a major contribution of EEX (e.g., BMK, MN15). It also includes range-separated hybrids (CAM-B3LYP, LC-BLYP). Similar error profiles of vertical energy were obtained for both dye groups, although the errors related to hydroxyphenylimidazopiridines are significantly larger. Overall, functionals including 40–55% of EEX (SOGGA11-X, BMK, M06-2X) ensure satisfactory agreement with the reference vertical excitation energies obtained using the RI-CC2 method; however, MN15 significantly outperforms them, providing a mean absolute error of merely 0.04 eV together with a very high correlation coefficient (R2 = 0.98). Within the investigated set of functionals, there is no single functional that would equally accurately determine ground- and excited-state dipole moments of difluoroboranes and hydroxyphenylimidazopiridine derivatives. Depending on the chosen set of dyes, the most accurate μGS predictions were delivered by MN15 incorporating a major EEX contribution (difluoroboranes) and by PBE0 containing a minor EEX fraction (hydroxyphenylimidazopiridines). Reverse trends are observed for μES, i.e., for difluoroboranes the best results were obtained with functionals including a minor fraction of EEX, specifically PBE0, while in the case of hydroxyphenylimidazopiridines, much more accurate predictions were provided by functionals incorporating a major EEX contribution (BMK, MN15).

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Section: Introductionmentioning

confidence: 99%

Benchmarking Density Functional Approximations for Excited-State Properties of Fluorescent Dyes

Grabarz

Ośmiałowski

2021

Molecules

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“…This intertwining AIDE behavior can be exploited for polarity sensing (Figure 5 , top right). [ 9a , 25 ]…”

Section: Resultsmentioning

confidence: 99%

Communication of Bichromophore Emission upon Aggregation – Aroyl‐S,N‐ketene Acetals as Multifunctional Sensor Merocyanines

Biesen

May

Nirmalananthan-Budau

et al. 2021

Chemistry A European J

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Aroyl-S,N-ketene acetal-based bichromophores can be readily synthesized in a consecutive three-component synthesis in good to excellent yields by condensation of aroyl chlorides and an N-(p-bromobenzyl) 2-methyl benzothiazolium salt followed by a Suzuki coupling, yielding a library of 31 bichromophoric fluorophores with substitution patterntunable emission properties. Varying both chromophores enables different communication pathways between the chromophores, exploiting aggregation-induced emission (AIE) and energy transfer (ET) properties, and thus, furnishing aggregation-based fluorescence switches. Possible applications range from fluorometric analysis of alcoholic beverages to pH sensors.

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“…BOD-CH3, on the other hand, exhibits the H-type aggregation resulting in the optically dark states. Solid-state luminescent materials based on BODIPY dyes with such a J-aggregation character have attracted broad attention [ 68–74 ].…”

Section: Boron-containing Compoundsmentioning

confidence: 99%

Molecular design and application of luminescent materials composed of group 13 elements with an aggregation-induced emission property

Ito

Gon

Tanaka

et al. 2021

National Science Review

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Complexation of π-conjugated ligands by metal or semimetal ions leads to the enhancement of the planarity and rigidity of the π-conjugated systems. Boron, especially, has played a central role in designing luminescent main-group complexes. However, these complexes still suffer the disadvantage of aggregation-caused quenching (ACQ) as well as typical organic fluorophores. It has recently been reported that some types of boron complexes exhibit the aggregation-induced emission (AIE) property. Moreover, the AIE behavior from the complexes and organometallic compounds composed of the other group 13 elements, such as aluminum and gallium, has emerged in this decade. These observations greatly encourage us to develop advanced functional materials based on the group 13 elements. Indeed, recent research has demonstrated that these classes of materials are potentially versatile scaffolds for constructing chromic luminophores, efficiently emissive π-conjugated polymers, and so on. This review mainly describes AIE-active group 13 complexes with four-coordinate structures and their applications as photo-functional materials. Proposed mechanisms of the origins of the AIE behavior are briefly discussed.

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Fine‐Tuning Dual Emission and Aggregation‐Induced Emission Switching in NPI–BODIPY Dyads

Cited by 87 publications

References 129 publications

Benchmarking Density Functional Approximations for Excited-State Properties of Fluorescent Dyes

Benchmarking Density Functional Approximations for Excited-State Properties of Fluorescent Dyes

Communication of Bichromophore Emission upon Aggregation – Aroyl‐S,N‐ketene Acetals as Multifunctional Sensor Merocyanines

Molecular design and application of luminescent materials composed of group 13 elements with an aggregation-induced emission property

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