Jean-Francois Morin

Jean-Francois Morin
Laval University | ULAVAL · Department of Chemistry

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93
Publications
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Publications

Publications (93)
Article
Linear and helical graphene nanoribbons (L-PyGNR and H-PyGNR) bearing electron-rich pyrrole units have been synthesized by using the photochemical cyclodehydrochlorination (CDHC) reaction. The pyrrole units in the polymer backbone make the polymer electron-rich with moderate bandgap values and relatively high HOMO energy levels. The planarization o...
Article
The solution‐phase synthesis is one of the most promising strategies for the preparation of well‐defined graphene nanoribbons (GNRs) in large scale. To prepare high quality, defect‐free GNRs, cycloaromatization reactions need to be very efficient, proceed without side reaction and mild enough to accommodate the presence of various functional groups...
Article
The solution-phase synthesis is one of the most promising strategies for the preparation of well-defined graphene nanoribbons (GNRs) in large scale. To prepare high quality, defect-free GNRs, cycloaromatization reactions need to be very efficient, proceed without side reaction and mild enough to accommodate the presence of various functional groups...
Article
Narrow thiophene-edged graphene nanoribbons (GNRs) were prepared from polychlorinated thiophene-containing poly(p-phenylene)s using the photochemical, metal-free cyclodehydrochlorination (CDHC) reaction. 1H NMR and Raman spectroscopy confirmed the structures of the GNRs. The regioselectivity of the CDHC reaction allows the preparation of both later...
Article
Narrow thiophene‐edged graphene nanoribbons (GNRs) were prepared from polychlorinated thiophene‐containing poly(p‐phenylene)s using the photochemical, metal‐free cyclodehydrochlorination (CDHC) reaction. 1H NMR and Raman spectroscopy confirmed the structures of the GNRs. The regioselectivity of the CDHC reaction allows the preparation of both later...
Article
Anthanthrone and its derivatives are large polycyclic aromatic compounds (PACs) that pose a number of challenges for incorporation into the structure of soluble conjugated polymers. For the first time, this group of PACs was employed as the building blocks for the synthesis of copolymers (P1-P5) based on poly[(arylene ethynylene)-alt-(arylene vinyl...
Article
Full-text available
Organic-based nanoparticles hold great potential for optoelectronics and biomedicine as they may provide optical properties in the visible range and notable advantages over inorganic counterparts. In this report, we exploit aggregation-induced emission (AIE) from the well-known tetraphenylethene (TPE) to yield photoluminescent polymer particles by...
Article
Alkanethiolates (ATs) forming self-assembled monolayers (SAMs) on coinage metal and semiconductor substrates have been used successfully for decades for tailoring the properties of these surfaces. Here, we provide a detailed analysis of a highly promising class of AT-based systems, which are modified by one or more dipolar carboxylic acid ester gro...
Article
Helicene-like graphene nanoribbons (HGNRs) are prepared through a regioselective photochemical cyclodehydrochlorination (CDHC) reaction from a polychlorinated polyphenylene precursor. In their Communication on page 6213 ff., J.-F. Morin and co-workers shown the HGNRs have a large band gap compared to other GNRs and are highly emissive. Such a well-...
Article
Nanobänder aus Helicen-artigem Graphen (HGNRs) wurden durch regioselektive photochemische Cyclodehydrochlorierung eines polychlorierten Polyphenylens synthetisiert. In ihrer Zuschrift (DOI: 10.1002/ange.201611834) zeigen J.-F. Morin und Mitarbeiter, dass die HGNRs stark leuchten und im Vergleich zu anderen GNRs eine große Bandlücke aufweisen. Solch...
Article
Carbon nanoparticles (CNPs) are promising materials for optoelectronic and biomedical applications thanks to their optical properties, low production cost, and superior biocompatibility compared to traditional semi-conductor quantum dots. The countless synthetic methods reported allow a library of diverse CNPs structures and optical properties, gui...
Article
Full-text available
A new alkyne-based macrocycle that combines monoyne, diyne and tetrayne is reported. Despite its unusual trapezoid shape, the bending of the tetrayne unit allows the macrocycle to be unstrained. The macrocycle is synthesized by a combination of selective deprotection of silylated alkyne, Castro–Stephen–Sonogashira coupling and copper-mediated oxida...
Article
Graphene is a zero-gap, semiconducting 2D material that exhibits outstanding charge-transport properties. One way to open a band gap and make graphene useful as a semiconducting material is to confine the electron delocalization in one dimension through the preparation of graphene nanoribbons (GNR). Although several methods have been reported so fa...
Article
Graphene is a zero-gap, semiconducting 2D material that exhibits outstanding charge-transport properties. One way to open a band gap and make graphene useful as a semiconducting material is to confine the electron delocalization in one dimension through the preparation of graphene nanoribbons (GNR). Although several methods have been reported so fa...
Chapter
This chapter presents a recent literature survey of both the intramolecular photochemical and direct CH arylation reactions to prepare polycyclic aromatic hydrocarbons (PAHs) and carbon nanomaterials fragments. The photochemical dehydrogenation, or Mallory reaction, is probably the most widely spread photochemical method for the preparation of carb...
Article
Novel nanographenes were prepared by a photochemical cyclodehydrochlorination (CDHC) reaction. Chlorinated precursors were irradiated in acetone in the presence of a base or in pure benzene and underwent multiple (up to four) regioselective cyclization reactions to provide rigid π-conjugated molecules. Pure compounds were recovered in good yields b...
Article
Novel nanographenes were prepared by a photochemical cyclodehydrochlorination (CDHC) reaction. Chlorinated precursors were irradiated in acetone in the presence of a base or in pure benzene and underwent multiple (up to four) regioselective cyclization reactions to provide rigid π-conjugated molecules. Pure compounds were recovered in good yields b...
Article
Five new copolymers based on the anthanthrone moiety were synthesized using Stille coupling. The anthanthrone unit was coupled with two electron-rich units (thiophene and carbazole) and three electron-poor units (thienopyrroledione, diketopyrrolopyrrole, and benzothiadiazole). The optoelectronics properties of the polymers were investigated and sug...
Article
Rhomboidal macrocyclic subunits of graphdiyne-like nanoribbon (GDNR) bearing both alkyne and diyne units, allowing for multi-channel pi-conjugation, were synthesized using oxidative Glaser-type ring closing reaction. These subunits, called the "meshes" of the nanoribbon, possess phenyl groups with decyloxy solubilizing chains on each corner. The yi...
Article
Super-extended tetrathiafulvalene compounds were prepared by the substitution of gem-dichlorovinylene with 1,2-benzenedithiol. This strategy allowed for the efficient synthesis of a highly π-extended 9,10-bis(benzo-1,3-dithiol-2-ylidene)-9,10-dihydroanthracene (sExTTF) moiety, which exhibits an intense light absorption in the visible spectrum and a...
Article
Six anthanthrene-based conjugated polymers with either electron-rich or electron-poor units were synthesized and characterized. All polymers exhibit optical absorption in the visible region owing to their extended conjugation. Experimental data and computational results indicate that the comonomer attached to the anthanthrene unit has only little e...
Article
With the intent of generating metallocavitands isostructural to species [(CpZr)3(μ(3)-O)(μ(2)-OH)3(κO,O,μ(2)-O2C(R))3](+), the reaction of Cp*2ZrCl2 and Cp*ZrCl3 with phenylcarboxylic acids was carried out. Depending on the reaction conditions, five new complexes were obtained, which consisted of Cp*2ZrCl(κ(2)-OOCPh) (1), (Cp*ZrCl(κ(2)-OOCPh))2(μ-κ...
Article
Full-text available
Dendrimers are monodisperse polymers grown in a fractal manner from a central point. They are poised to become the cornerstone of nanoscale devices in several fields, ranging from biomedicine to light-harvesting. Technical difficulties in obtaining these molecules has slowed their transfer from academia to industry. In 2001, the arrival of the "cli...
Article
Full-text available
Anthanthrene small molecules with different pendant groups were investigated as semiconductors for organic field-effect transistors and solar cells. Field-effect mobilities were greatly improved with solvent annealing and reached maximum values of 0.078 cm2V-1s-1 for a thiophene-appended anthanthrene derivative. When used as donors in conjunction w...
Article
Rational design of meta-linked oligophenylbutadiynylene (OPBDs) derivatives has been conducted in order to gain insights on their gelation properties and reactivity toward topochemical polymerization to yield polydiacetylenes (PDAs). Different structural parameters influencing the gel formation such as the presence of peripheral 2-hydroxyethoxy sid...
Article
Full-text available
The synthesis and self-assembly of two new phenylacetylene macrocycle (PAM) organogelators were performed. Polar 2-hydroxyethoxy side chains were incorporated in the inner part of the macrocycles to modify the assembly mode in the gel state. With this modification, it was possible to increase the reactivity of the macrocycles in the xerogel state t...
Article
Full-text available
Since the aggregation-induced emission (AIE) phenomenon is very sensitive to steric hindrance, we set out to use it as a tool to probe the periphery of dendrimers. To achieve this, dendrimers with an ethylene oxide (EO) core were synthesized and then decorated with AIE-active units. Tetraphenylethylene (TPE) with varying spacer lengths was used as...
Article
A new series of exTTF hosts has been synthesized for supramolecular binding study of fullerenes C60 and C70. Binding constants for C60 in chlorobenzene, toluene, toluene-CH2Cl2 and CS2 have been calculated for different hosts and a direct structure-affinity relationship has been established. As predicted, receptors with two exTTF moieties (, and )...
Article
The synthesis and spectroscopic characterization of zirconium(IV) dicarboxylate 1 and metallocavitand 2 are described. Encapsulation studies of fullerenes C-60 and C-70 were performed using UV-Vis spectroscopy in chlorobenzene, toluene, benzene, carbon disulfide and in a mixture of toluene/dichloromethane. UV-Vis titrations have shown that the bind...
Article
A series of ferrocene-based statistical copolymers have been prepared via radical polymerization and their nanoporous structure was characterized using inert gas adsorption-desorption isotherms and high resolution transmission electron microscopy (HRTEM). The porosity parameters of the polymers were obtained by physisorption isotherms (N-2 at -196...
Article
A series of 6,12-bis(amino) anthanthrene-based conjugated molecules were prepared and characterized using UV–vis and fluorescence spectroscopy and cyclic voltammetry. The absorption spectra and redox potentials of these molecules can be modulated by changing the conjugated moieties linked at the 4 and 10 positions. Moreover, the optoelectronic prop...
Article
Pyrolysis of polydiacetylene-walled nanorods obtained from a rigid and shape-persistent macrocyclic precursor was performed. The thermogravimetric analysis showed that pyrolysis caused a loss of aliphatic chains and structural changes of PDAs to produce carbon-rich nanoarchitectures, as confirmed by Raman and UV-visible spectroscopy. The transmissi...
Article
A series of zirconium-carboxylate metallocavitands with the general formula [(CpZr)3(μ-κ2,O',O″CR)3(μ3-O)(μ2-OH)3]Cl (Cp = cyclopentadienyl; R = C5H4N (5), C6H7N (6), C18H14N (7), and C18H12N (8)) were synthesized in moderate to high yields (40-83%) by reacting the corresponding carboxylic acids 1-4 with Cp2ZrCl2 in a self-assembly procedure at roo...
Article
An efficient and versatile synthetic strategy toward cruciform anthanthrene compounds was developed using Sonogashira couplings steps. Acetylenic linkers were used to effectively extend the pi-conjugation of polycyclic anthanthrone and anthanthrene compounds and tune their opto-electronic properties. Structure-property relationships supported by DF...
Article
Full-text available
A layered graphitic material was prepared from an alkyne-containing, reactive molecular precursor at low temperature without catalyst. The resulting nanomaterial is made of stacks of a few partially graphitized nanosheets and is soluble in common organic solvents in which it exhibits green fluorescence.
Article
Carbon nanomaterials have been the subject of intense research over the past 20 years. Both the physical and all-organic methods used to prepare them possess advantages and drawbacks regarding purity, batch-to-batch uniformity, large-scale production, and conditions of preparation. In this account, we present an overview of ‘hybrid methods’, in whi...
Article
A series of 6,12-bis(amino) anthanthrene-based conjugated molecules was prepared and characterized using UV-visible and fluorescence spectroscopy and cyclic voltammetry. The modulation of the absorption spectra and redox potentials of these molecules is possible by changing the conjugated moieties linked at the 4 and 10 positions. Moreover, the opt...
Article
The preparation of carbon nanomaterials has been the focus of many research groups over the last twenty years. Traditionally, the synthesis of these materials has been accomplished using physical methods involving harsh conditions, limiting their applicability in numerous technological areas. Thus, researchers have been constantly working on develo...
Article
Rigid organic nanotubes were prepared from six-membered phenylene-butadiynylene macrocycles through topochemical polymerization in the xerogel state. All six butadiyne units underwent polymerization, thus creating rigid nanotubes with six polydiacetylene chains lying parallel, one relative to each other.
Article
Full-text available
Two series of amide-containing phenylacetylene macrocycles (PAMs) were prepared and self-assembled through a gelation process in an organic solvent. Their gelation properties along with their molecular arrangements in the xerogel state, their morphological features and their reactivity toward the topochemical polymerization of the butadiyne units e...
Article
A star-shaped molecule with three butadiyne moieties attached to a central phenyl core was self-assembled via organogel formation in different solvents and subjected to UV irradiation in its xerogels form to give a soluble conjugated 1D nanowire made of three connected polydiacetylene (PDA) chains. The resulting polymer has a slightly lower optical...
Article
New p-type, n-type, and ambipolar molecules were synthesized from commercially available 4,10-dibromoanthanthrone dye. Substitution at the 4,10- and 6,12-positions with different electron-rich and electron-poor units allowed the modulation of the optoelectronic properties of the molecules. A bis(dicyanovinylene)-functionalized compound was also pre...
Article
Soluble organic nanorods were prepared from phenylacetylene macrocycles using the topochemical polymerization of butadiyne moieties placed both inside and outside the macrocycles' skeleton. Macrocycles containing amide groups were self-assembled in a columnar fashion through the formation of an organogel in ethyl acetate. Upon irradiation with UV l...
Article
We report the synthesis and characterization of tantalum-boronate trimetallic clusters of general formula {[Cp*Ta](3)(μ(2)-RB(O)(2))(3)(μ(2)-OH)(μ(2)-O)(2)(μ(3)-OH)} (R= 4-(C(6)H(5))(C(6)H(4)) (Ta(3)-4Ph), 4-(C(6)H(5)O)(C(6)H(4)) (Ta(3)-4OPh), 4-(C(7)H(7)O)(C(6)H(4)) (Ta(3)-4OBn), 4-(C(8)H(5))(C(6)H(4)) (Ta(3)-4PhEt), and 4-(C(12)H(7))(C(6)H(4)) (T...
Article
Synthetic efforts toward the preparation of rotaxane precursors based on phenylacetylene macrocycles (PAM) are described. The aim of this study was to determine the optimal structural parameters to prepare high-molecular-weight rotaxane precursors through a strategy involving two Sonogashira couplings to attach bulky blockers on the PAM core. PAMs...
Article
Full-text available
Carbon nanoparticles were obtained at room temperature by irradiating an organogel made from a 1,8-diaryloctatetrayne derivative in chloroform. During the topochemical polymerization, the morphology of the gel changes from fibers to soluble, yellow fluorescent nanoparticles in high yield. Analyses suggest that the resulting nanoparticles are made o...
Article
Third and fourth generation ethylene oxide-containing dendrimers containing triazole units were prepared divergently through metal-free Huisgen 1,3-dipolar cycloaddition (“click”) reaction between activated disubstituted alkyne and terminal azide groups. The growth of the dendrimers was achieved in high yield with minimal purification effort and wi...
Article
Full-text available
New strapped porphyrin-based hosts with different π-conjugated moieties and linkers have been prepared and their ability to bind with fullerenes was studied in dilute solution. We found that the ability of these hosts to bind with fullerenes strongly depends on their chemical nature and more precisely on the substitution pattern of the porphyrin de...
Article
We report the synthetic proof-of-concept for a three-faced particle based on a PAMAM dendrimer in which each face bears a different labile protecting group. This new strategy yields a controlled, well-defined and monodisperse dendrimer. To achieve this, a tri-orthogonal strategy was employed through Sonogashira coupling and Cu(I)-catalyzed Huisgen...
Article
A new soluble C60 derivative bearing a diketopyrrolopyrrole (DPP) moiety has been synthesized by ethynylation reaction. Characterization by UV-visible spectrophotometry and cyclic voltammetry has been performed in order to study the influence of the DPP moiety on electronic and optical properties of the fullerene. Moreover, DFT calculations have be...
Article
Full-text available
An amide-containing phenylacetylene macrocycle (PAM) has been synthesized and its gelation properties were studied in different solvents. Surprisingly, this macrocycle forms organogels at low concentration in many polar and apolar solvents. XRD and FTIR analysis suggest that this macrocycle forms stable supramolecular assemblies owing to H-bonding....
Article
Eight new ethynyl-bridged fullerene derivatives with different substituents (referred to as the "secondary group") in the $alpha$-position relative to the alkyne have been prepared in order to study the ability of the secondary group to modulate their electrochemical properties, especially the LUMO energy level, of C60. These new materials have bee...
Article
A diarylbutadiyne derivative was synthesized using a few steps and gelified in aromatic solvents. The gel prepared at low concentration is made of micrometers-long nanofibrils as shown by scanning electron microscopy. XRD of the dried gel shows sharp features, revealing a well-organized material. A topochemical reaction was performed on the dried g...
Article
The synthesis of a new class of π-conjugated based on N-alkyl-2,7-carbazole is reported. Two different synthetic pathways were used to obtain 2,7-functionalized carbazole units. The first pathway leads to N-alkyl-2,7-dichlorocarbazole which undergoes a Yamamoto coupling to obtain the homopolymer. The second synthetic method provides N-alkyl-2,7-dii...
Article
A new series of soluble C60 derivatives for organic electronic application has been synthesized by ethynylation reaction using different electron-donating and electron-withdrawing groups of varying length.Graphical abstract
Article
A series of eight rotors containing thiol groups for attachment to gold surfaces and fluorine atoms for solid-state 19F NMR spectroscopy have been prepared through linear, multistep synthesis. The common rotating part of the rotors (rotator), consisting of a 2,6-difluorobenzene moiety, is introduced into the rotor structure through an unusual regio...
Chapter
This first systematic compilation of synthesis methods for different classes of polymers describes well-tested and reproducible procedures, thus saving time, money and chemicals. Each chapter presents the latest method for a specific class of conjugated polymers with a particular emphasis on the design aspects for organo-electronic applications. In...
Article
Full-text available
The number of synthetic methods enabling the preparation of ammonium-based rotaxanes has increased very rapidly in the past ten years. The challenge in the synthesis of rotaxanes results from the rather weak interactions between the ammonium-containing rod and the crown ether macrocycle in the pseudorotaxane structure that rely mostly on O*H hydrog...
Article
The synthesis of new [2]- and [3]rotaxanes through Sonogashira coupling has been accomplished in the aim to built oligo(phenyleneethynylene) (OPE) encircled by crown ethers. Optimization of the Sonogashira coupling for the formation of the [2]rotaxane (capping reaction) is presented and the best method has been applied for the synthesis of the long...
Article
A series of dendronized diblock copolymers having rigid backbone and reactive surface were synthesized by ring-opening metathesis polymerization (ROMP) from dendronized norbornene derivatives using the second generation Grubb's catalyst. The bromine-terminated block of those rigid nanostructures has been converted to more reactive azide groups in o...
Article
Full-text available
Multimodal agents that serve as both probes for contrast and light-activated effectors of cellular processes in diseased tissue were developed. These agents were introduced into multicellular tumor spheroids (3D tissue models) and in the chorioallantoic membrane (CAM) of a chicken embryo. The luminescence decay was examined using a novel technique...
Article
Full-text available
The effect of a magnetic field on the steady-state and time-resolved optical emission of a custom fullerene-linked photosensitizer (PS) in liposome cell phantoms was studied at various oxygen concentrations (0.19-190 microM). Zeeman splitting of the triplet state and hyperfine coupling, which control intersystem crossing between singlet and triplet...
Article
Surface immobilization of pristine C60 by supramolecular interactions is an attractive way to introduce C60 on surfaces since the pi-electron network and the electronic properties of C60 remain intact. Several hosts have been developed for surface complexation of C60. With few exceptions, the hosts reported to date are "electronically inert", limit...
Article
The development of multimodal molecular probes and photosensitizing agents for use in photodynamic therapy (PDT) is vital for optimizing and monitoring cytotoxic responses. We propose a combinatorial approach utilizing photosensitizing molecules that are both paramagnetic and luminescent with multimodal functionality to perturb, control, and monito...
Article
A new supramolecular host with good affinity toward fullerenes has been developed. This host having a tweezer-like shape is built on a [3]rotaxane scaffold and contains two free-base porphyrin moieties as recognition units for fullerenes. The ability of this tweezer to bind fullerenes strongly depends on the solvent system used and the size of full...
Article
A new set of aryleneethynylene derivatives bearing three, four, and six p-carboranes as potential wheels attached to a semirigid chassis have been designed and synthesized. These molecules are expected to move in predetermined patterns on atomically smooth surfaces, depending on their specific configuration.
Conference Paper
To build up true molecular machines and understand the mechanics of nanoscale motion and manipulation in molecular system, we have created and investigated a family of molecules based around the concept of the nanocar, which has the rolling wheels made of spherical fullerene or carborane molecules. Assisted by scanning tunneling microscopy (STM), w...
Article
We report the synthesis of a new nanovehicle, a porphyrin-based nanotruck. The porphyrin inner core was designed for possible transportation of metals and small molecules across a surface.
Article
Full-text available
Nanovehicles are a new class of molecular machines consisting of a molecular scale chassis, axles, and wheels, that can roll across solid surfaces with structurally defined directions making them of interest to synthetic chemists, surface scientists, chemical engineers, and the general car enthusiast. In this tutorial review, following a brief intr...
Article
New electroactive and photoactive conjugated copolymers consisting of alternating 2,7-carbazole and oligothiophene moieties linked by vinylene groups have been developed. Different oligothiophene units have been introduced to study the relationship between the polymer structure and the electronic properties. The resulting copolymers are characteriz...
Article
[structure: see text] With the eventual goal of demonstrating a motorized nanocar, the key structure has been synthesized which bears a light-activated unidirectional molecular motor and an oligo(phenylene ethynylene) chassis and axle system with four carboranes to serve as the wheels. Kinetics studies in solution show that the motor indeed rotates...
Article
Design, syntheses, and testing of new, fullerene-wheeled single molecular nanomachines, namely, nanocars and nanotrucks, are presented. These nanovehicles are composed of three basic components that include spherical fullerene wheels, freely rotating alkynyl axles, and a molecular chassis. The use of spherical wheels based on C60 and freely rotatin...
Article
We have fabricated organic field-effect transistors based on thin films of 2,7-carbazole oligomeric semiconductors 1,4-bis(vinylene-(N-hexyl-2-carbazole))phenylene (CPC), 1,4-bis(vinylene-(N′-methyl-7′-hexyl-2′-carbazole))benzene (RCPCR), N-hexyl-2,7-bis(vinylene-(N-hexyl-2-carbazole))carbazole (CCC), and N-methyl-2,7-bis(vinylene-(7-hexyl-N-methyl...
Article
A theoretical and experimental study of the structure, optical and photophysical properties of 2,7-carbazolenevinylene-based derivatives in solution were presented. The density functional theory was used to carry put geometry optimizations of the ground states of PCP, PCP-CN and TCT-CN. It was found that the PCP and TCT were nearly planar in their...
Article
Carbazole-based oligomeric and polymeric materials have been studied for almost 25 years for their unique electrical electrochemical and optical properties. Interestingly, carbazole units can be linked in two different ways leading to either poly(3,6 carbazole) or poly(2,7 carbazole) derivatives. While the former class seems to be very interesting...