One Step Synthesis of Polythiophenes from the Partially Purified Crude Extract of the Roots of Tagetes Erecta

Abstract

Polythiophene and its derivatives are valuable conjugated polymers due to their physical properties and applications in various fields. Precursors of polythiophenes were conventionally obtained from petrochemical byproducts, which are non-renewable. Thiophene and its derivatives had been found naturally in Tagetes species such as Tagetes erecta, Tagetes tenuifolia, etc. Tagetes species produce 2, 2':5', 2''-terthienyl (Alpha-T), 5-(3-buten-1-ynyl)-2, 20-bithienyl (BBT), 5-(4-hydroxy-1-butynyl)-2, 20-bithienyl (BBTOH), and 5-(4-acetoxy-1-butynyl)-2, 20-bithienyl (BBTOAc), which are accumulated in different parts, specifically in the roots of the plants. These thiophene derivatives were extracted and identified by GC-MS, Uv-vis, FTIR and TLC analysis. The partially purified plant extract is polymerized through one step oxidative free radical polymerization to obtain polythiophenes. Product characterization has revealed that the selective polymerization of thiophene derivatives results in the phase-separated end product from the rest of the materials in the plant-extract.

Phytochemical Screening and Antibacterial Activity of Taxus baccata L. against Pectobacterium spp. and Dickeya chrysanthemi

“…The bands at ca. 1460, 1245, 790, and 779 cm −1 show the connectivity of thiophene rings through 2,5 coupling [27]. The bands at 2849, 1409, 1255, and 1193 cm −1 have been previously reported for methyl D-lyxopyranosides [28]; those at 1143, 1023, 918, and 865 cm −1 for dioxolanes [29]; and those at 2915, 1698, and 1102 cm −1 for hydroxycyclopentenones [30].…”

“…DC. [20]), identified in the extracts presented herein, may have the antimicrobial activity preconized for other thiophene derivatives [27,34,35]. It has been reported that thiophene acetylenes (such as 10,11-erythro-xanthopappin D) possess bioactivity against P. carotovorum, with an MIC of 7.25 µg•mL −1 [36].…”

2,5-Diisopropenylthiophene by Suzuki–Miyaura cross-coupling reaction and its exploitation in inverse vulcanization: a case study

“…On the other hand, the S- r -DIT samples show spectra which retain the features of the thiophene ring and methyl groups of the starting DIT. Indeed, the vibration so-called of ring breathing and that due to the out-of-plane heteroaromatic = C–H wagging at, respectively, 1453 and 799 cm −1 , related to the presence of a 2,5-disubstituted thiophene moiety, 49,50 are still observable, indicating the thiophene ring is maintained as such in the macromolecular architecture obtained upon IV reaction. It may be useful to recall here the typical signal of CC olefinic double bond does not appear as such in thiophene moiety.…”

Study on Thiophenes Extraction Efficacy From Tagetes Patula L.

“…The total thiophenes concentration varies with species, organ, harvesting period (Kodithuwakku, et al 2016), while the compounds distribution varies as well and is represented by combinations of polythiophenes as the ones mentioned in the table above: α-T, BBT, PBT, BBTOH, BBT(OAc)2 and other compounds. For optimal extraction yields, the technological steps should include conditions avoiding light exposure, as thiophenes biological activity is photosensitive (Deineka, et al 2014).…”

“…The identified methods of analysis in the literature mention the possibilities of photodegradation and volatilization, thus it is recommended to manipulate the extracts in low light intensity conditions (as well as conditioning them in brown or opaque recipients) and to carefully monitor the temperature in extraction and concentration steps. The identification and quantification analyses include chromatographic separation techniques such as GC-MS (Margl, Tei, et al 2001); (Szarka, et al 2006); (Saha and Walia 2012), HPLC (Deineka, et al 2014); (Zannah, Cahyana and Saefumillah 2021); (Vijayta, Shanker and ur Rahman 2015) and HPTLC (Deineka, et al 2014) or spectrometric techniques such as FTIR (Kodithuwakku, et al 2016) and UV-VIS (Kodithuwakku, et al 2016).…”