Benzochalcogendiazole-based conjugated molecules: investigating the effects of substituents and heteroatom juggling

Patel, Heta A.; Bhanvadia, Viraj J.; Mande, Hemant M.; Zade, Sanjio S.; Patel, Arun L.

doi:10.1039/c9ob01762c

Cited by 14 publications

(11 citation statements)

References 77 publications

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“…Patel et al . also observed the dimerization of benzoselenadizole moiety through strong Se−N interaction with d Se−N of 3.00‐3.43 Å [60] …”

Section: ‘2e−2n Square’mentioning

confidence: 80%

“…I believe this review will give a clear idea on the designing of molecular materials having benzochalcogenodiazole to explore the material behavior and packing pattern by tuning the chalcogen bonding ability. SÀ N 3.35 [51] 2.90 [50] SeÀ N 3.43 [60] 2.57 [61,62] TeÀ N 2.94 [70] 2.25 [74]…”

Section: Discussionmentioning

confidence: 99%

“…Patel et al also observed the dimerization of benzoselenadizole moiety through strong SeÀ N interaction with d SeÀ N of 3.00-3.43 Å. [60] During early 2009 Goumont et al reported supramolecular assemblies by co-crystalizing benzoselenadiazole and N-alkylated cationic benzoselanadiazole (BDS 10). In solid state a supramolecular trimer was formed through two asymmetric SeÀ N interactions with d SeÀ N of 2.573 Å and 2.967 Å (Figure 9b).…”

Section: He Received Phd From Indian Institute Of Science Education A...mentioning

confidence: 99%

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‘2E−2N squares’: Chalcogen (E=S, Se and Te) Bonding Involving Benzochalcogenodiazoles

Pati

2023

Asian J Org Chem

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Several intra and intermolecular interactions (secondary bonding interactions, SBIs) such as halogen bonding (XB), hydrogen bonding (HB) have great impact on crystal engineering, from catalysis to material and pharmaceutical applications. With respect to other interactions chalcogen (S, Se and Te) bonding (ChB) is less explored until very recently, although it has great potential to evolve in larger domain. In literature there are several reports on ChB and their roles in solid‐state packing of molecular materials having benzochalcogenodiazole as an active moiety applicable in organic electronics. Some important and informative reviews on ChB and their various applications in catalysis and structural properties relationship were also presented. Here purpose of this review is to summarize the ChB involved in π‐conjugated molecular system having benzochalcogenodiazole to form ‘2E−2N square’ which seems to be very important supramolecular synthon involving ChB.

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“…Patel et al . also observed the dimerization of benzoselenadizole moiety through strong Se−N interaction with d Se−N of 3.00‐3.43 Å [60] …”

Section: ‘2e−2n Square’mentioning

confidence: 80%

Section: Discussionmentioning

confidence: 99%

Section: He Received Phd From Indian Institute Of Science Education A...mentioning

confidence: 99%

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‘2E−2N squares’: Chalcogen (E=S, Se and Te) Bonding Involving Benzochalcogenodiazoles

Pati

2023

Asian J Org Chem

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“…108 [139], 109 [140], 110 [137] and 111 [141]. The prototypal tape for this series is shown in The exceptional tape is found in the crystal of 111, with end-and side-on views illustrated in Fig.…”

Section: Tapes Featuring Se … N Interactionsmentioning

confidence: 99%

Supramolecular aggregation patterns featuring Se⋯N secondary-bonding interactions in mono-nuclear selenium compounds: A comparison with their congeners

Tiekink

2021

Coordination Chemistry Reviews

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An evaluation of the Cambridge Structural Database for crystals containing Se … N secondary--bonding interactions was conducted. The presence of Se … N secondary-bonding interactions has been established in nearly 9% of crystals of mono-nuclear selenium compounds where such interactions can potentially form, that is, having at least one nitrogen atom. The Se … N interactions feature in 71 zero-dimensional, usually di-nuclear aggregates, 63 one-dimensional chains and tapes, and smaller numbers of two-and three-dimensional arrays, that is seven and one, respectively. Selenium(II) compounds form the majority of the dataset with only eight selenium(IV) compounds included in the survey. In most cases (112 out of 142), the selenium centre forms a single Se … N contact with 26 aggregates having a selenium atom forming two contacts and four examples where three Se … N contacts are evident. The great propensity of selenadiazole rings (75%) and selenocyanates (50%) to form Se … N secondary-bonding interactions in their crystals is particularly noteworthy.

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“…[6] In addition, BTD derivatives were successfully synthesized by the double Heck crosscoupling reaction in Patel's group. [7] The successful synthesis of BTD derivatives offered the possibility of future development as fluorescent probes for NIR-II or photodynamic therapy. The absorption and emission spectra of BTD-based compounds appeared red-shifted compared to benzoxadiazole compounds, because BTD could reduce the band gap more effectively.…”

Section: Introductionmentioning

confidence: 99%

π‐Extended BTD Derivatives: Synthesis, Photophysical Properties, and Applications in Biological Systems Imaging for Discriminating Living and Dead Cells

Cao

Wang

et al. 2023

Chemistry An Asian Journal

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Here, π‐Extended BTD derivatives were successfully synthesized by Heck coupling reaction, which exhibited the the advantages of simplicity and efficiency, wild substrate scope, easily available substrates and high yield. The fluorescent probe PEG‐BTDAr targeting LDs was successfully prepared by the nucleophilic substitution reaction between the Heck coupling reaction product 3 h and Amino polyethylene glycol monomethyl ether (Mn=2000). PEG‐BTDAr exhibited the advantages of high selectivity, good stability and pH resistance. The use of PEG as a substrate gave PEG‐BTDAr good biocompatibility. It was worth mentioning that PEG‐BTDAr could not only track LDs in cells under different physiological conditions, but also distinguish between living and dead cells in biological systems.

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Benzochalcogendiazole-based conjugated molecules: investigating the effects of substituents and heteroatom juggling

Abstract: A range of benzochalcogendiazole-based small molecules are synthesized following various C–C coupling methodologies and studied for their photo-physical properties and structural aspects.

Cited by 14 publications

References 77 publications

‘2E−2N squares’: Chalcogen (E=S, Se and Te) Bonding Involving Benzochalcogenodiazoles

‘2E−2N squares’: Chalcogen (E=S, Se and Te) Bonding Involving Benzochalcogenodiazoles

Supramolecular aggregation patterns featuring Se⋯N secondary-bonding interactions in mono-nuclear selenium compounds: A comparison with their congeners

π‐Extended BTD Derivatives: Synthesis, Photophysical Properties, and Applications in Biological Systems Imaging for Discriminating Living and Dead Cells

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