Synthesis of a Fluorescent Conjugated Polymer in the Undergraduate Organic Teaching Laboratory

Abstract

Fluorescent organic polymers are used in a wide range of applications, including explosive sensing, clean energy technologies, and biological detection schemes. However, such polymers are rarely synthesized in an undergraduate organic teaching laboratory due to their air and moisture sensitivity. The synthesis of a fluorescent organic polymer, poly[2-methoxy-5-(2ethylhexyloxy)-1,4-phenylenevinylene] (MEH-PPV), is described for the upper-division undergraduate organic laboratory. This polymerization is accomplished using straightforward procedures to exclude air and moisture, without requiring the use of a glovebox or strict inert-atmosphere conditions. Once synthesized, the polymer is used for two applications, the fabrication of fluorescent thin films and the formation of organic conjugated nanoparticles, and leads to a number of pedagogical opportunities about polymerization, organic fluorescence, solid-state properties, and hydrophobic nanoparticle formation.

Environmental Application of Cyclodextrin Metal–Organic Frameworks in an Undergraduate Teaching Laboratory

“…The students in the study were part of an advanced organic laboratory, but the multidisciplinary nature of this project makes it a suitable project for other advanced laboratories in environmental and analytical chemistry. Moreover, we note that this experiment complements our previously published laboratory experiments in this Journal in the synthesis and analysis of near-infrared squaraine fluorophores and of fluorescent organic polymers, , in that these three experiments, in conjunction with any of the numerous material science laboratory experiments published in this Journal , − can be used as the basis for a semester-long laboratory course on materials chemistry.…”

“…Previous reports from our group have detailed the implementation of two new experiments in such an advanced laboratory setting: the synthesis and photophysical characterization of a near-infrared emitting squaraine dye, 28 and the synthesis, characterization, and thin film fabrication of a highly fluorescent conjugated polymer. 29 Both of these multiday experiments start with a synthetic organic chemistry component, followed by analysis of the newly obtained organic product. The interdisciplinary components of these experiments include photophysical analyses of the products (for both the squaraine and the polymer), incorporation of the polymer into thin films and nanoparticles, and analysis of how aggregation due to different polymer presentations/manifestations affects the resultant photophysical properties.…”

“…Senior-level undergraduate laboratory classes for chemistry majors provide a unique opportunity to implement laboratory curricula focused on issues beyond the four traditional disciplines, including interdisciplinary experiments with an environmental focus. Previous reports from our group have detailed the implementation of two new experiments in such an advanced laboratory setting: the synthesis and photophysical characterization of a near-infrared emitting squaraine dye, and the synthesis, characterization, and thin film fabrication of a highly fluorescent conjugated polymer . Both of these multiday experiments start with a synthetic organic chemistry component, followed by analysis of the newly obtained organic product.…”

Design, Implementation, and Evaluation of Paper-Based Devices for the Detection of Acetaminophen and Phenacetin in an Advanced Undergraduate Laboratory

“…To address this gap between significant interdisciplinary work in the chemical enterprise and less interdisciplinary undergraduate chemistry education, our laboratory has developed a number of new experiments for the undergraduate teaching laboratory that have a strong interdisciplinary focus and substantial pedagogical advantages. In particular, we have previously reported the synthesis and analysis of a nearinfrared emitting squaraine fluorophore; 10 the synthesis and characterization of a fluorescent conjugated polymer and the subsequent fabrication of nanoparticles and thin films; 11 and the synthesis, analysis, and practical applications of a cyclodextrin-containing metal−organic framework for environmental pollutant removal. 12 In continuation of our goals to create relevant and interdisciplinary experiments for undergraduate teaching laboratories, we focused next on the area of colorimetric chemical detection, an active research topic in our own group.…”

A self-healable fluorescence active hydrogel based on ionic block copolymers prepared via ring opening polymerization and xanthate mediated RAFT polymerization

“…Recently fluorescent active hydrogels have been developed for use in several applications due to their optical response 8 , which can be utilized in drug delivery systems, glucose sensors 9,10 , thermoresponsive sensors 11 , insulin sensors 12 , and real time monitoring of the hydrogel behaviour like deformation, movement, degradation, fluorescence guided monitoring of surgery etc [13][14][15][16][17] . Many fluorescent materials such as conjugated conductive polymers 18,19 , fluorescent nanoparticles (i.e Ag NPs) 20,21 , fluorescent organic nanoparticles (FONs) 22 , carbon quantum dots (QDs),nanodots [23][24][25] and fluorescent dyes 26 are used to incorporate luminescent properties in the polymeric hydrogel system. However these materials suffer from several issues including: (i) high probability of aggregation of the nanodots or nano materials, resulting in self-quenching of fluorescence (ii) leaching of the nano materials can cause a toxic effect on the environment and (iii) the low structural stability in the presence of physical and chemical impacts.…”