3-Pyridylvinyl benzoxazole-derived multifunctional organic materials—from solid-state photoreactivity to photophysical and electrochemical properties

Baskar, Shyamvarnan; Kole, Goutam Kumar

doi:10.1039/d4nj00190g

New J. Chem.

2024

DOI: 10.1039/d4nj00190g

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3-Pyridylvinyl benzoxazole-derived multifunctional organic materials—from solid-state photoreactivity to photophysical and electrochemical properties

Shyamvarnan Baskar,

Goutam Kumar Kole

Abstract: Development of multifunctional organic materials is the current thirst area of research in organic materials chemistry. This study reports synthesis, crystal structure elucidation and multiple property investigation of E-3-pyridylvinyl benzoxazole...

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2024

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Cited by 2 publications

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9-Phenanthrenylvinyl-4′-pyridine and Its N-Methylated Analogue: From the Crystal Structure and Photoisomerization to Photophysical and Electrochemical Properties and Application in Bioimaging

Kannan,

Yadav,

Rukmini Sarma

et al. 2024

Crystal Growth & Design

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Designing novel functional compounds is a key step in coordination and organic materials chemistry. Herein, 9phenanthrenylvinyl-4′-pyridine (9-PheVP), as a new ligand, has been synthesized and structurally characterized for the first time, along with its N-methylated analogue (9-MPheVP). Both compounds have been explored for their photophysical and redox properties and their applicability in bioimaging. The effect of quaternization on the crystal structure, absorption, emission, and redox properties has been investigated. Bathochromic and hypochromic shifts were observed in the absorption and emission properties upon quaternization. Both neutral and cationic compounds showed large Stokes shifts of 9250 and 8000 cm −1 , respectively. 9-MPheVP was observed to photoisomerize in the solid state to its cis-configuration (9-MPheVP-cis) upon exposure to light. Crystal structure determination of 9-MPheVP-cis revealed that with Z′ = 2, it represents a rare class of crystals for which Z′ > 1. The utility of 9-MPheVP as an efficient ligand has also been established by structurally characterizing a silver(I) complex, [Ag(9-PheVP) 2 ]BF 4 . Our results show that 9-PheVP can serve as a promising ligand in coordination chemistry and offers a platform for developing multifunctional organic materials.

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9-Phenanthrenylvinyl-4′-pyridine and Its N-Methylated Analogue: From the Crystal Structure and Photoisomerization to Photophysical and Electrochemical Properties and Application in Bioimaging

Kannan,

Yadav,

Rukmini Sarma

et al. 2024

Crystal Growth & Design

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Ag(I)···π-Influenced, Anion-Controlled Structural Variation in Coordination Networks of E-3-Pyridylvinyl Benzoxazole: Sunlight-Driven Regioselective Photodimerization in the Solid State

Baskar,

Kole

2024

Crystal Growth & Design

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The coordination chemistry of the flexible N-donor ligand E-3-pyridylvinyl benzoxazole (3-PVBO) with various silver salts has been investigated for the first time. Four novel coordination compounds of silver, have been synthesized and structurally characterized. 3-PVBO adopts two different configurations, i.e., syn-and anti-, and offers structural variation in the series with different anions. In both 1 and 2, it adopts syn-configuration, and thus, 16-membered metallacycles are formed. In 3, with the trifluoroacetate anion, it adopts anticonfiguration, and thus, a zigzag 1D coordination polymeric network is formed. However, in 4 with the SbF 6 − anion, despite it adopting the syn-configuration, instead of a metallacycle, a 1D coordination polymeric network is observed. More interestingly, 3-PVBO ligands were found to stack parallel in 3 and 4, suitable for the photodimerization reaction in the solid state. 3 exhibited photodimerization in the head-to-tail fashion, leading to the formation of the coordination polymer, {[Ag(rctt-HT-PBOCB)(CF 3 CO 2 )]} ∞ 2 (5), where PBOCB = 1,3-bis(benzoxazole)-2,4-bis(3′-pyridyl) cyclobutane. However, 4 underwent photodimerization in the head-to-head fashion. Thus, varying the anions achieved a regioselective synthesis of functional cyclobutane derivatives. No argentophilic but Ag(I)•••π interaction was observed in this series.

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3-Pyridylvinyl benzoxazole-derived multifunctional organic materials—from solid-state photoreactivity to photophysical and electrochemical properties

Abstract: Development of multifunctional organic materials is the current thirst area of research in organic materials chemistry. This study reports synthesis, crystal structure elucidation and multiple property investigation of E-3-pyridylvinyl benzoxazole...

Cited by 2 publications

References 102 publications

9-Phenanthrenylvinyl-4′-pyridine and Its N-Methylated Analogue: From the Crystal Structure and Photoisomerization to Photophysical and Electrochemical Properties and Application in Bioimaging

9-Phenanthrenylvinyl-4′-pyridine and Its N-Methylated Analogue: From the Crystal Structure and Photoisomerization to Photophysical and Electrochemical Properties and Application in Bioimaging

Ag(I)···π-Influenced, Anion-Controlled Structural Variation in Coordination Networks of E-3-Pyridylvinyl Benzoxazole: Sunlight-Driven Regioselective Photodimerization in the Solid State

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