Hydrogen‐Bonding Induced Alternate Stacking of Donor (D) and Acceptor (A) Chromophores and their Supramolecular Switching to Segregated States

This paper reports comprehensive studies on the mixed assembly of bis‐(trialkoxybenzamide)‐functionalized dialkoxynaphthalene (DAN) donors and naphthalene‐diimide (NDI) acceptors due the cooperative effects of hydrogen bonding, charge‐transfer (CT) interactions, and solvophobic effects. A series of DAN as well as NDI building blocks have been examined (wherein the relative distance between the two amide groups in a particular chromophore is the variable structural parameter) to understand the structure‐dependent variation in mode of supramolecular assembly and morphology (organogel, reverse vesicle, etc.) of the self‐assembled material. Interestingly, it was observed that when the amide functionalities are introduced to enhance the self‐assembly propensity, the mode of co‐assembly among the DAN and NDI chromophores no longer remained trivial and was dictated by a relatively stronger hydrogen‐bonding interaction instead of a weak CT interaction. Consequently, in a highly non‐polar solvent like methylcyclohexane (MCH), although kinetically controlled CT‐gelation was initially noticed, within a few hours the system sacrificed the CT‐interaction and switched over to the more stable self‐sorted gel to maximize the gain in enthalpy from the hydrogen‐bonding interaction. In contrast, in a relatively less non‐polar solvent such as tetrachloroethylene (TCE), in which the strength of hydrogen bonding is inherently weak, the contribution of the CT interaction also had to be accounted for along with hydrogen bonding leading to a stable CT‐state in the gel or solution phase. The stability and morphology of the CT complex and rate of supramolecular switching (from CT to segregated state) were found to be greatly influenced by subtle structural variation of the building blocks, solvent polarity, and the DAN/NDI ratio. For example, in a given D–A pair, by introducing just one methylene unit in the spacer segment of either of the building blocks a complete change in the mode of co‐assembly (CT state or segregated state) and the morphology (1D fiber to 2D reverse vesicle) was observed. The role of solvent polarity, structural variation, and D/A ratio on the nature of co‐assembly, morphology, and the unprecedented supramolecular‐switching phenomenon have been studied by detail spectroscopic and microscopic experiments in a gel as well as in the solution state and are well supported by DFT calculations.     

Biocatalytic Self‐Assembly of Supramolecular Charge‐Transfer Nanostructures Based on n‐Type Semiconductor‐Appended Peptides

The reversible in situ formation of a self‐assembly building block (naphthalenediimide (NDI)–dipeptide conjugate) by enzymatic condensation of NDI‐functionalized tyrosine ( NDI‐Y ) and phenylalanine‐amide ( F‐NH₂ ) to form NDI‐YF‐NH₂ is described. This coupled biocatalytic condensation/assembly approach is thermodynamically driven and gives rise to nanostructures with optimized supramolecular interactions as evidenced by substantial aggregation induced emission upon assembly. Furthermore, in the presence of di‐hydroxy/alkoxy naphthalene donors, efficient charge‐transfer complexes are produced. The dynamic formation of NDI‐YF‐NH₂ and electronic and H‐bonding interactions are analyzed and characterized by different methods. Microscopy (TEM and AFM) and rheology are used to characterize the formed nanostructures. Dynamic nanostructures, whose formation and function are driven by free‐energy minimization, are inherently self‐healing and provide opportunities for the development of aqueous adaptive nanotechnology.     

Hydrogen‐Bonding‐Mediated Vesicular Assembly of Functionalized Naphthalene–Diimide‐Based Bolaamphiphile and Guest‐Induced Gelation in Water

This paper describes the spontaneous vesicular assembly of a naphthalene–diimide (NDI)‐based non‐ionic bolaamphiphile in aqueous medium by using the synergistic effects of π‐stacking and hydrogen bonding. Site isolation of the hydrogen‐bonding functionality (hydrazide), a strategy that has been adopted so elegantly in nature, has been executed in this system to protect these moieties from the bulk water so that the distinct role of hydrogen bonding in the self‐assembly of hydrazide‐functionalized NDI building blocks could be realized, even in aqueous solution. Furthermore, the electron‐deficient NDI‐based bolaamphiphile could engage in donor–acceptor (D–A) charge‐transfer (CT) interactions with a water‐insoluble electron‐rich pyrene donor by virtue of intercalation of the latter chromophore in between two NDI building blocks. Remarkably, even when pyrene was located between two NDI blocks, intermolecular hydrogen‐bonding networks between the NDI‐linked hydrazide groups could be retained. However, time‐dependent AFM studies revealed that the radius of curvature of the alternately stacked D–A assembly increased significantly, thereby leading to intervesicular fusion, which eventually resulted in rupturing of the membrane to form 1D fibers. Such 2D‐to‐1D morphological transition produced CT‐mediated hydrogels at relatively higher concentrations. Instead of pyrene, when a water‐soluble carboxylate‐functionalized pyrene derivative was used as the intercalator, non‐covalent tunable in‐situ surface‐functionalization could be achieved, as evidenced by the zeta‐potential measurements.     

Hydrogen-Bonding Induced Alternate Stacking of Donor (D) and Acceptor (A) Chromophores and their Supramolecular Switching to Segregated States

This paper reports comprehensive studies on the mixed assembly of bis-(trialkoxybenzamide)-functionalized dialkoxynaphthalene (DAN) donors and naphthalene-diimide (NDI) acceptors due the cooperative effects of hydrogen bonding, charge-transfer (CT) interactions, and solvophobic effects. A series of DAN as well as NDI building blocks have been examined (wherein the relative distance between the two amide groups in a particular chromophore is the variable structural parameter) to understand the structure-dependent variation in mode of supramolecular assembly and morphology (organogel, reverse vesicle, etc.) of the self-assembled material. Interestingly, it was observed that when the amide functionalities are introduced to enhance the self-assembly propensity, the mode of co-assembly among the DAN and NDI chromophores no longer remained trivial and was dictated by a relatively stronger hydrogen-bonding interaction instead of a weak CT interaction. Consequently, in a highly non-polar solvent like methylcyclohexane (MCH), although kinetically controlled CT-gelation was initially noticed, within a few hours the system sacrificed the CT-interaction and switched over to the more stable self-sorted gel to maximize the gain in enthalpy from the hydrogen-bonding interaction. In contrast, in a relatively less non-polar solvent such as tetrachloroethylene (TCE), in which the strength of hydrogen bonding is inherently weak, the contribution of the CT interaction also had to be accounted for along with hydrogen bonding leading to a stable CT-state in the gel or solution phase. The stability and morphology of the CT complex and rate of supramolecular switching (from CT to segregated state) were found to be greatly influenced by subtle structural variation of the building blocks, solvent polarity, and the DAN/NDI ratio. For example, in a given D-A pair, by introducing just one methylene unit in the spacer segment of either of the building blocks a complete change in the mode of co-assembly (CT state or segregated state) and the morphology (1D fiber to 2D reverse vesicle) was observed. The role of solvent polarity, structural variation, and D/A ratio on the nature of co-assembly, morphology, and the unprecedented supramolecular-switching phenomenon have been studied by detail spectroscopic and microscopic experiments in a gel as well as in the solution state and are well supported by DFT calculations.     

Self‐Assembly of Carboxylic Acid Appended Naphthalene Diimide Derivatives with Tunable Luminescent Color and Electrical Conductivity

Self‐assembly of a series of carboxylic acid‐functionalized naphthalene diimide (NDI) chromophores with a varying number (n=1–4) of methylene spacers between the NDI ring and the carboxylic acid group has been studied. The derivatives show pronounced aggregation due to the synergistic effects of H‐bonding between the carboxylic acid groups in a syn–syn catemer motif and π stacking between the NDI chromophores. Solvent‐dependent UV/Vis studies reveal the existence of monomeric dye molecules in a “good” solvent such as chloroform and self‐assembly in “bad” solvents such as methylcyclohexane. The propensity of self‐assembly is comparable for all samples. Temperature‐dependent spectroscopic studies show high thermal stability of the H‐bonding‐mediated self‐assembled structures. In the presence of a protic solvent such as MeOH, self‐assembly can be suppressed, suggesting a decisive role of H‐bonding, whereas π stacking is more a consequence of than a cause for self‐assembly. Syn–syn catemer‐type H‐bonding is supported by powder XRD studies and the results corroborate well with DFT calculations. The morphology as determined by AFM is found to be dependent on the value of n; with increasing n, the morphology gradually shifts from 2D nanosheets to 1D nanofibers. Emission spectra show sharp emission bands with relatively small Stokes shifts. In addition, a rather broad emission band is observed at longer wavelengths because of the in situ formation of excimer‐type species. Due to such a heterogeneous nature, the emission spectrum spans almost the entire red–green–blue region. Depending on the value of n, the ratio of intensities of the two emission bands is changed, which results in a tunable luminescent color. Furthermore, in the case of n=1 and 3, almost pure white light emission is observed. Time‐resolved photoluminescence spectra show a very short lifetime (a few picoseconds) of monomeric dye molecules and biexponential decays with longer lifetimes (on the order of nanoseconds) for aggregated species. Current–voltage measurements show electrical conductivity in the range of 10^?4 S cm^?1 for the aggregated chromophores, which is four orders of magnitude higher than the value for a structurally similar NDI control molecule lacking the H‐bonding functionality.     

Side chain engineering of naphthalene diimide–bithiophene‐based polymer acceptors in all‐polymer solar cells

Two novel polymeric acceptors based on naphthalene diimide (NDI) and 2.2′‐bithiophene, named as P(NDI2THD‐T2) and P(NDI2TOD‐T2), were designed and synthesized for all polymer solar cells application. The structural and electronic properties of the two acceptors were modulated through side‐chain engineering of the NDI units. The optoelectronic properties of the polymers and the morphologies of the blend films composed of the polymer acceptors and a donor polymer PTB7‐Th were systemically investigated. With thiophene groups introduced into the side chains of the NDI units, both polymers showed wider absorption from 350 nm to 900 nm, compared with the reference polymer acceptor of N2200. No redshift of absorption spectra from solutions to films indicated reduced aggregation of the polymers due to the steric hindrance effect of thiophene rings in the side chains. The photovoltaic performance were characterized for devices in a configuration of ITO/PEDOT:PSS/PTB7‐Th:acceptors/2,9‐bis(3‐(dimethylamino)propyl)anthra[2,1,9‐def:6,5,10‐def]diisoquinoline‐1,3,8,10(2H,9H)‐tetraone (PDIN)/Al. With the addition of diphenyl ether as an additive, the power conversion efficiencies (PCEs) of 2.73% and 4.75% for P(NDI2THD‐T2) and P(NDI2TOD‐T2) based devices were achieved, respectively. The latter showed improved J_sc, Fill Factor (FF), and PCE compared with N2200 based devices. © 2017 Wiley Periodicals, Inc. J. Polym. Sci., Part A: Polym. Chem. 2017 , 55, 3679–3689     

One donor–two acceptor (D–A1)‐(D–A2) random terpolymers containing perylene diimide,naphthalene diimide,and carbazole units

A series of one donor–two acceptor (D–A₁)‐(D–A₂) random terpolymers containing a 2,7‐carbazole donor and varying compositions of perylene diimide (PDI) and naphthalene diimide (NDI) acceptors was synthesized via Suzuki coupling polymerization. The optical properties of the terpolymers are weighted sums of the constituent parent copolymers and all show strong absorption over the 400 to 700 nm range with optical bandgaps ranging from 1.77 to 1.87 eV, depending on acceptor composition. The copolymers were tested as acceptor materials in bulk heterojunction all‐polymer solar cells using poly[(4,8‐bis‐(2‐ethylhexyloxy)‐benzo[1,2‐b;4,5‐b′]dithiophene)‐2,6‐diyl‐alt‐(4‐(2‐ethylhexanoyl)‐thieno[3,4‐b]thiophene)‐2,6‐diyl] (PBDTTT‐C) as the donor material. In contrast to the optoelectronic properties, the measured device parameters are not composition dependent, and rather depend solely on the presence of the NDI unit, where the devices containing any amount of NDI perform half as well as those using the parent polymer containing only carbazole and PDI. Overall this is the first example of a one donor–two acceptor random terpolymer system containing perylene diimide (PDI) and naphthalene diimide (NDI) acceptor units, and demonstrates a facile method of tuning polymer optoelectronic properties while minimizing the need for complicated synthetic and purification steps. © 2014 Wiley Periodicals, Inc. J. Polym. Sci., Part A: Polym. Chem. 2014 , 52, 3337–3345     

Stimuli‐Responsive Self‐Assembly of a Naphthalene Diimide by Orthogonal Hydrogen Bonding and Its Coassembly with a Pyrene Derivative by a Pseudo‐Intramolecular Charge‐Transfer Interaction

A naphthalene diimide (NDI) building block containing hydrazide (H1) and hydroxy (H2) groups self‐assembled into a reverse‐vesicular structure in methylcyclohexane by orthogonal H‐bonding and π‐stacking. At an elevated temperature (LCST=43 °C), destruction of the assembled structure owing to selective dissociation of H2–H2 H bonding led to macroscopic precipitation. Further heating resulted in homogeneous redispersion of the sample at 70 °C (UCST) and the formation of a reverse‐micellar structure. In the presence of a pyridine (H3)‐functionalized pyrene (PY) donor, a supramolecular dyad (NDI–PY) was formed by H2–H3 H‐bonding. Slow transformation into an alternate NDI–PY stack occurred by a folding process due to the charge‐transfer interaction between NDI and PY. The mixed NDI–PY assembly exhibited a morphology transition from a reverse micelle (with a NDI–PY mixed‐stack core) below the LCST to another reverse micelle (with a NDI core) above the UCST via a “denatured” intermediate.     

Di­aqua­(sulfato‐κO)[2,4,6‐tris(2‐pyridyl)‐1,3,5‐triazine‐κ3N1,N2,N6]zinc(II) dihydrate

In the title compound, [Zn(SO₄)(C₁₈H₁₂N₆)(H₂O)₂]·2H₂O, the metal complex is monomeric, with an octahedral Zn^II centre coordinated by the tridentate ligand 2,4,6‐tris(2‐pyridyl)‐1,3,5‐triazine (tpt), two aqua mol­ecules and a monodentate sulfate ion. A complex hydrogen‐bonding scheme is built up out of the profuse availability of donors and acceptors (O—H⋯O/N and C—H⋯O) which, in addition to π–π interactions between tpt groups, define a three‐dimensional assembly.     

Donors and acceptors based on triangular dehydrobenzo[12]annulenes: formation of a triple-layered rosette structure by a charge-transfer complex

We present here the results of studies of the synthesis and properties of donors and acceptors based on triangular dehydrobenzo[12]annulene ([12]DBA) system as a pi core. These studies were aimed at controlling the supramolecular crystal structure. Toward this end, the tricyano[12]DBA 2 and dodecafluoro[12]DBA ( 3) were synthesized as acceptors (A) and the tris(dialkylamino)[12]DBAs 4a-d as donors (D), and their electronic properties were determined by electronic absorption spectroscopy and electrochemical measurements. The main focus, though, was the formation of supramolecular structures in crystals. These compounds form distinct packing patterns as a result of the different intermolecular interactions. Tricyano[12]DBA 2 forms a two-dimensional (2D) sheet structure via hydrogen-bonding interactions, whereas a tilted-stack structure was found for 3 because of the lack of significant intermolecular interactions. Tris(dibutylamino)[12]DBA 4b exhibits a ladder-type 2D structure, probably because of van der Waals interactions between the butyl groups. The most significant finding is that charge-transfer interactions between donor 4a and acceptor 3 combined with their triangular molecular shapes and lateral CH...F hydrogen bonding result in the formation of a 2D rosette structure consisting of two different trimeric (DAD- and ADA-type) sandwich structures with 1:2 and 2:1 A/D ratios, respectively.     

盐酸介导策略合成的具有优异光催化能力的ZnFe2O4小颗粒点缀一维苝二酰亚胺S型异质结

由于有机材料的结构多样性,越来越多的研究者选择有机材料作为光催化剂.典型的n型有机半导体花二酰亚胺(PDI)不仅在可见光照射下有较强的光响应能力,而且有合适的带隙和负导带,使得光激发电子具有较强的还原能力.半导体光催化剂的适用性受到光生载流子复合的限制,而构建S型异质结可有效保证电荷分离,也可保证空穴和电子的强氧化能力...     

Exploring Crystal Structure in Ethyne‐Substituted Pentacenes,and Their Elaboration into Crystalline Dehydro[18]annulenes

Approaches to control the self‐assembly of aromatic structures to enhance intermolecular electronic coupling are the key to the development of new electronic and photonic materials. Acenes in particular have proven simple to functionalize to induce strong π‐stacking interactions, although finer control of intermolecular π‐overlap has proven more difficult to accomplish. In this report, we describe how very weak hydrogen bonding interactions can exert profound impact on solid‐state order in solubilized pentacenes, inducing self‐assembly in either head‐to‐tail motifs with strong 2‐D π‐stacking, or head‐to‐head orientations with much weaker, 1‐D π‐stacking arrangements. In order to achieve 3‐D π‐stacking useful for photovoltaic applications, we elaborated a series of diethynyl pentacenes to their trimeric dehydro[18]annulene forms. These large, strongly interacting structures did indeed behave as acceptors in polymer photovoltaic devices.     

Hydrogen-bonding-mediated vesicular assembly of functionalized naphthalene-diimide-based bolaamphiphile and guest-induced gelation in water

This paper describes the spontaneous vesicular assembly of a naphthalene-diimide (NDI)-based non-ionic bolaamphiphile in aqueous medium by using the synergistic effects of π-stacking and hydrogen bonding. Site isolation of the hydrogen-bonding functionality (hydrazide), a strategy that has been adopted so elegantly in nature, has been executed in this system to protect these moieties from the bulk water so that the distinct role of hydrogen bonding in the self-assembly of hydrazide-functionalized NDI building blocks could be realized, even in aqueous solution. Furthermore, the electron-deficient NDI-based bolaamphiphile could engage in donor-acceptor (D-A) charge-transfer (CT) interactions with a water-insoluble electron-rich pyrene donor by virtue of intercalation of the latter chromophore in between two NDI building blocks. Remarkably, even when pyrene was located between two NDI blocks, intermolecular hydrogen-bonding networks between the NDI-linked hydrazide groups could be retained. However, time-dependent AFM studies revealed that the radius of curvature of the alternately stacked D-A assembly increased significantly, thereby leading to intervesicular fusion, which eventually resulted in rupturing of the membrane to form 1D fibers. Such 2D-to-1D morphological transition produced CT-mediated hydrogels at relatively higher concentrations. Instead of pyrene, when a water-soluble carboxylate-functionalized pyrene derivative was used as the intercalator, non-covalent tunable in-situ surface-functionalization could be achieved, as evidenced by the zeta-potential measurements.     

Self‐assembly of H‐bonded side‐chain and cross‐linking copolymers containing diblock‐copolymeric donors and single/double H‐bonded light‐emitting acceptors

A series of diblock‐copolymers were synthesized through anionic polymerization of styrene and tert‐butyl methacrylate (tBuA) with different monomer ratios, and analogous block‐copolymeric derivatives (PS‐b‐PAA)s with monofunctional carboxylic acid groups were obtained by further hydrolyzation as hydrogen‐bonded (H‐bonded) proton donors. Via H‐bonded interaction, these diblock‐coplymeric donors (PS‐b‐PAA)s were incorporated with luminescent mono‐pyridyl/bis‐pyridyl acceptors to form single/double H‐bonded supramolecules, that is, H‐bonded side‐chain/cross‐linking copolymers, respectively. The supramolecular architectures formed by donor polymers and light‐emitting acceptors were influenced by the ratio of acid blocks in the diblock copolymeric donors and the type of single/double H‐bonded light‐emitting acceptors. Their thermal and luminescent properties can be adjusted by H‐bonds, and more than 100 nm of red‐shifted photoluminescence (PL) emissions were observed, which depend on the degrees of the H‐bonding interactions. Self‐assembled phenomena of amphiphilic dibolck copolymers and their H‐bonded complexes were confirmed by TEM micrographs, and supramolecular microphase separation of spherical micelle‐like morphology was demonstrated to affect the photophysical properties. Polymer light‐emitting diode (PLED) devices containing H‐bonded complexes showed electroluminescence (EL) emissions of 503–560 nm under turn‐on voltages of 7.5–9.0 V, maximum power efficiencies of 0.23–0.37 cd/A (at 100 mA/cm²), and maximum luminances of 318–519 cd/m² (around 25 V). © 2009 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem 47: 4685–4702, 2009     

Charge and Spin Transport in an Organic Molecular Square

Understanding electronic communication among multiple chromophoric and redox units requires construction of well‐defined molecular architectures. Herein, we report the modular synthesis of a shape‐persistent chiral organic square composed of four naphthalene‐1,8:4,5‐bis(dicarboximide) (NDI) sides and four trans‐1,2‐cyclohexanediamine corners. Single crystal X‐ray diffraction reveals some distortion of the cyclohexane chair conformation in the solid state. Analysis of the packing of the molecular squares reveals the formation of highly ordered, one‐dimensional tubular superstructures, held together by means of multiple [C H⋅⋅⋅OC] hydrogen‐bonding interactions. Steady‐state and time‐resolved electronic spectroscopies show strong excited‐state interactions in both the singlet and triplet manifolds. Electron paramagnetic resonance (EPR) and electron‐nuclear double resonance (ENDOR) spectroscopies on the monoreduced state reveal electron sharing between all four NDI subunits comprising the molecular square.     

Supramolecularly Engineered Amphiphilic Macromolecules: Molecular Interaction Overrules Packing Parameters

We report molecular interaction‐driven self‐assembly of supramolecularly engineered amphiphilic macromolecules (SEAM) containing a single supramolecular structure‐directing unit (SSDU) consisting of an H‐bonding group connected to a naphthalene diimide chromophore. Two such SEAMs, P1‐50 and P2‐50, having the identical chemical structure and hydrophobic/hydrophilic balance, exhibit distinct self‐assembled structures (polymersome and cylindrical micelle, respectively) due to a difference in the H‐bonding group (hydrazide or amide, respectively) of the single SSDU. When mixed together, P1‐50 and P2‐50 adopted self‐sorted assembly. For either series of polymers, variation in the hydrophobic/hydrophilic balance does not alter the morphology reconfirming that self‐assembly is primarily driven by directional molecular interaction which is capable of overruling the existing norms in packing parameter‐dependent morphology control in an immiscibility‐driven block copolymer assembly.     

Crystal Engineering of Dual Channel p/n Organic Semiconductors by Complementary Hydrogen Bonding

The supramolecular arrangement of organic semiconductors in the solid state is as critical for their device properties as the molecular structure, but is much more difficult to control. To enable supramolecular design of semiconducting materials, we introduced dipyrrolopyridine as a new donor semiconductor capable of complementary hydogen bonding with naphthalenediimide acceptors. Through a combination of solution, crystallographic, and device studies, we show that the self‐assembly driven by H bonding a) modulates the charge‐transfer interactions between the donor and acceptor, b) allows for precise control over the solid‐state packing, and c) leads to a combination of the charge‐transport properties of the individual components. The predictive power of this approach was demonstrated in the synthesis of three new coassembled materials which show both hole and electron transport in single‐crystal field‐effect transistors. These studies provide a foundation for advanced solid‐state engineering in organic electronics, capitalizing on the complementary H bonding.     

Fluoride ion sensing by an anion-π interaction

We report the discovery of a supramolecular interaction (anion-π and charge/electron transfer, CT/ET) involving fluoride ion and π-electron deficient colorless naphthalene diimide (NDI) receptors. Strong electronic interactions between lone-pair electrons of F(-) ion and π*-orbitals of the NDI unit lead to an unprecedented F(-)→NDI ET event, which produces an orange colored NDI(?-) radical anion. Further reduction of NDI(?-) by another F(-) ion produces a pink colored NDI(2-) dianion, rendering NDI a colorimetric F(-) sensor. Preorganization of two NDI units in overlapping positions using folded linkers improves their selectivity and sensitivity for the F(-) ion significantly, allowing F(-) detection at nM concentration in 85:15 DMSO/H(2)O solutions.     

Hydrogen‐Bonding‐Regulated Supramolecular Nanostructures and Impact on Multivalent Binding

Herein we describe the H‐bonding‐regulated nanostructure, thermodynamics, and multivalent binding of two bolaamphiphiles NDI‐1 and NDI‐2 consisting of a hydrophobic naphthalene diimide connected to a hydrophilic wedge by a H‐bonding group and a glucose moiety on its two arms. NDI‐1 and NDI‐2 differ by the single H‐bonding group, namely, hydrazide or amide, which triggers the formation of vesicles and cylindrical micelles, respectively. Although the extended H‐bonding ensures stacking with head‐to‐head orientation and the formation of an array of the appended glucose moieties in both systems, the adaptive cylindrical structure exhibited superior multivalent binding with concanavalin A (ConA) to that of the vesicle. A control amphiphile lacking a H‐bonding group assembled with a random lateral orientation to produce spherical micelles without any notable multivalent binding.     

Perylene and naphthalene diimide copolymers for all-polymer solar cells: Effect of perylene/naphthalene ratio

We report the synthesis of a series of copolymers, having 2,2′-bithiophene as electron-donating moiety, and perylene diimide (PDI) and/or naphthalene diimide (NDI) as electron-accepting moiety, and employed as non-fullerene acceptors in polymer solar cells (PSCs). All the copolymers show wide absorption varying from 300 to 850 nm in the visible and NIR spectrum. When changing the PDI/NDI ratio in the polymer backbone, The LUMO energy levels vary in the range of −3.90 to −3.80 eV and the HOMO energy levels vary in the range of −6.10 to −5.85 eV. Among PSCs based on PTB7-Th donor and these polymer acceptors, the devices based on PTB7-Th/NDI100 yield the best power conversion efficiency (PCE) of 4.67%, while the PTB7-Th/PDI100-based devices yield a PCE of 1.03%. © 2016 Wiley Periodicals, Inc. J. Polym. Sci., Part A: Polym. Chem. 2017 , 55, 682–689