Synthesis of Dimeric Imidazo[1, 5‐<i>a</i>]pyridines and Their Photophysical Properties

Yagishita, Fumitoshi; Kozai, Natsumi; Nii, Chiho; Tezuka, Yoshihiko; Uemura, Naohiro; Yoshida, Yasushi; Mino, Takashi; Sakamoto, Masami; Kawamura, Yasuhiko

doi:10.1002/slct.201702277

Cited by 11 publications

(6 citation statements)

References 45 publications

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“…Other different applications have been reported for multi‐ impy products such as bioimaging or therapeutic agents under UVA‐LED irradiation conditions [86–88] . In this case, the tested products show a potential application as photodynamic therapy agents against tumour cells (F. Yagishita et al.…”

Section: Discussionmentioning

confidence: 99%

“…Other different applications have been reported for multiimpy products such as bioimaging or therapeutic agents under UVA-LED irradiation conditions. [86][87][88] In this case, the tested products show a potential application as photodynamic therapy agents against tumour cells (F. Yagishita et al reported the use of UVA-LED λexc = 365 nm, 1.1 W as a light source). [86] In general, a multi-impy nucleus has been successfully prepared [89,90] showing similar chelating behaviours in compar-ison to the most investigated poly-pyridines or multibipyridines.…”

Section: Multi-impy Skeletonmentioning

confidence: 99%

See 1 more Smart Citation

Luminescent Imidazo[1,5‐a]pyridine Scaffold: Synthetic Heterocyclization Strategies‐Overview and Promising Applications

Volpi

2022

Asian J Org Chem

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In the last few years, imidazo[1,5‐a]pyridine derivatives have attracted growing attention due to their remarkable emissive behaviours, structural modification and biological properties. Previously published works emphasize the possible technological applications of this luminescent scaffold and demonstrate the stringent relationship between chemical substituents and optical properties. The main goal of this work is to provide a complete list of the reported achievements concerning these promising heterocyclization reactions obtained starting from a huge variety of reagents, catalysts, oxidants, dehydrating agents involved in various reaction conditions. Particular attention is focused on the final possible substitutions, conjugations and structural modifications of the reported synthetic approaches, a powerful aspect to design innovative and employable new luminescent imidazo[1,5‐a]pyridine products.

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Section: Discussionmentioning

confidence: 99%

Section: Multi-impy Skeletonmentioning

confidence: 99%

Luminescent Imidazo[1,5‐a]pyridine Scaffold: Synthetic Heterocyclization Strategies‐Overview and Promising Applications

Volpi

2022

Asian J Org Chem

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“…All compounds were synthetized following the literature procedures. 21,23,36,[51][52][53][54] A list of the solvents employed for crystallization and the conditions of synthesis of each polymorph can be found in Table 1.…”

Section: Synthesismentioning

confidence: 99%

Polymorphism and solid state peculiarities in imidazo[1,5-a]pyridine core deriving compounds: An analysis of energetic and structural driving forces

Priola

Conterosito

Volpi

et al. 2022

Journal of Molecular Structure

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The polymorphism and solid-state peculiarities of imidazo [1,5-a]pyridine derivatives have been investigated by a theoretical and experimental approach to shed light on the structural and energetic features of this family. Four couples of polymorphs and an ionic crystal form have been reported and analysed. Hirshfeld Surface and Energy Frameworks have been used to better understand the crystal packing features, in comparison with literature structures. The collection of all these characterizations made possible to analyse the differences between the polymorphs, the main energetic component dominating the crystal packing, and the effect of the different substitution on the central molecular skeleton on packing disposition. The assignment of vibrational spectra for the imidazo[1,5a]pyridine core has been performed for the first time. Although the discussed polymorphs are very different in their crystal packing, from the energetic point of view they present a strong similarity. In all cases, the main interactions are π‧‧‧π stacking and C-H‧‧‧π to the aromatic rings, with some tendency to the formation of C-H‧‧‧N contacts to the central imidazo [1,5a]pyridine nitrogen. The main energetic component is the dispersive one, with some contribution from the electrostatic component, and this situation is not modified by the presence of differing substituents. When hydrogen bond are present, the crystal packing is strongly modified and, energetically, the electrostatic component can overcome the dispersive on.

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“…N-Heteroacenes are capable of recognizing Brønsteda cids through the lone-pair electrons of the imino Natoms, which are characteristic of Lewis-basic sp 2 -hybridized orbitals. [18][19][20][21][22][23] We previously reportedt hat a p-conjugated liquid that was composed of an N-heteroacene framework respondedt oH Cl vapor,t hereby resultingi nad ramatic change in the color of its photoluminescence. [15] Herein, we report the synthesis of an ew stimuli-responsive p-conjugated liquid (1) that was composed of an N-heteroacene framework with finely tuned electronic properties as well as acid-responsive capabilities.…”

Section: Introductionmentioning

confidence: 98%

“…With the aim of developing a series of new functional fluidic liquids, we focused on the N‐heteroacene framework, in which C atoms in a π‐conjugated hydrocarbon are partially replaced by imino N atoms. N‐Heteroacenes are capable of recognizing Brønsted acids through the lone‐pair electrons of the imino N atoms, which are characteristic of Lewis‐basic sp 2 ‐hybridized orbitals . We previously reported that a π‐conjugated liquid that was composed of an N‐heteroacene framework responded to HCl vapor, thereby resulting in a dramatic change in the color of its photoluminescence .…”

Section: Introductionmentioning

confidence: 99%

Tuning the Electronic Properties and Acid‐Response Behavior of N‐Heteroacene‐Based π‐Conjugated Liquids by Changing the Number of π‐Conjugated Substituents

Sato

Mutoh

Matsukuma

et al. 2018

Chemistry An Asian Journal

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We have designed and synthesized two room-temperature-fluorescent π-conjugated liquids based on the N-heteroacene framework (1 and 2). These two π-conjugated liquids, which contained one and two thiophene rings, respectively, exhibited different electronic properties and rheology behaviors. Single-crystal X-ray analysis of dithiophene-appended compound 4 revealed that two thiophene rings hindered the interactions of the imino N atoms with acids through the formation of interactions between the S atoms of the thiophene rings and the imino N atoms of the pyrazine group. On the other hand, monothiophene-appended molecules 1 and 3 each contained an unhindered imino N atom on the opposite site to the thiophene ring. Upon dissolving various acids with different pK values in compounds 1 and 2, these slight structural differences gave rise to marked differences in their acid-response behaviors, thereby resulting in the emission of variously colored fluorescence in the liquid state. Furthermore, when acids with lower pK values was dissolved in compounds 1 and 2, phase transition occurred from an isotropic liquid state to a self-organized liquid-crystalline phase.

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Synthesis of Dimeric Imidazo[1, 5‐a]pyridines and Their Photophysical Properties

Cited by 11 publications

References 45 publications

Luminescent Imidazo[1,5‐a]pyridine Scaffold: Synthetic Heterocyclization Strategies‐Overview and Promising Applications

Luminescent Imidazo[1,5‐a]pyridine Scaffold: Synthetic Heterocyclization Strategies‐Overview and Promising Applications

Polymorphism and solid state peculiarities in imidazo[1,5-a]pyridine core deriving compounds: An analysis of energetic and structural driving forces

Tuning the Electronic Properties and Acid‐Response Behavior of N‐Heteroacene‐Based π‐Conjugated Liquids by Changing the Number of π‐Conjugated Substituents

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