Croconic Acid Integrated Zwitterionic Conjugated Porous Polymer for Effective Iodine Adsorption.

Given the rapid growth of the nuclear sector, effective treatment of radioactive iodine is critical. Herein, we report the synthesis and the iodine adsorption properties of croconic acid (CTPB) and squaric acid (STPB) containing π-conjugated novel zwitterionic conjugated porous polymers (CPPs). The CPPs have been synthesized through a condensation reaction of tris(4-aminophenyl)benzene with croconic acid or squaric acid in high yields (~95 %).

A croconic acid-derived narrow band gap conjugated microporous polymer.

Croconic acid, a novel highly electron-deficient building block, was introduced into a conjugated microporous polymer (CTPA). The CMP possesses strong donor-acceptor interactions, which resulted in near-IR absorption (red edge ∼1350 nm), a narrow bandgap (<1 eV) and high electrical conductivity upon doping (0.1 S m).

A Two-Dimensional Poly(azatriangulene) Covalent Organic Framework with Semiconducting and Paramagnetic States.

The black crystalline (aza)triangulene-based covalent organic framework was synthesized from its trinitro-TANG precursor via a one-pot, two-step reaction involving Pd-catalyzed hydrogenation and polycondensation with an aromatic dialdehyde. High crystallinity and permanent porosity of the layered two-dimensional (2D) structure were established. The rigid, electron-rich trioxaazatriangulene (TANG) building block enables strong π-electron interactions manifested in broad absorptions across the visible and NIR regions ( ≈ 1.

Dimension-controlled assemblies of anion-responsive π-electronic systems bearing aryl substituents with fan-shaped geometries.

Pyrrole-4-aryl-substituted dipyrrolyldiketone BF complexes as anion-responsive π-electronic molecules were synthesized via a 3,5-dimethylpyrrole precursor. Mesophases were observed in derivatives that possessed long alkyl chains on the pyrrole-4-aryl groups along with their anion complexes as ion-pairing assemblies in combination with appropriate cations.

Halogenated boron-dipyrromethenes: synthesis, properties and applications.

Boron-dipyrromethene dyes (BODIPYs) containing halogens at pyrrole carbons are very useful synthons for the synthesis of a variety of BOIDPYs for a wide range of applications. Among the functional groups, halogens are the functional groups which can be regiospecifically introduced at any desired pyrrole carbon of the BODIPY framework by adopting appropriate synthetic strategies. The halogenated BODIPYs can undergo facile nucleophilic substitution reactions to prepare several interesting BODIPY based compounds.

Axially bonded pentads constructed on the Sn(IV) porphyrin scaffold.

Three covalently linked dyads such as porphyrin-ferrocene, porphyrin-BODIPY and porphyrin-sapphyrin containing one hydroxyphenyl group at the meso-position of porphyrin were synthesized by coupling the trans-functionalized porphyrin building block, 5-(4-hydroxyphenyl)-10-(4-iodophenyl)-15,20-diphenyl porphyrin, with the ethynyl functionalized redox/chromophore building block under mild Pd(0) coupling conditions. The dyads were then reacted with SnTTP(OH)2 in benzene in a 2 : 1 ratio at reflux temperature for 12 hours followed by simple alumina column chromatographic purification which afforded three pentads containing three different types of redox/chromophore components in 62-80% yields. The pentads are very stable and freely soluble in all common organic solvents.

Synthesis of conjugated BODIPYs via the Wittig reaction.

A Wittig reaction was employed to synthesize conjugated BODIPYs in high yields by treating formylated BODIPYs with alkyl/aryl ylides under simple room temperature conditions. Treatment of 3,5-diformyl BODIPYs or α-formyl 3-pyrrolyl BODIPY with different alkyl/aryl ylides in CH2Cl2 at room temperature for 2 h followed by straightforward column chromatographic purification on silica afforded conjugated BODIPYs in ~65-90% yields. This is an alternate method to Knoevenagel and Heck reactions which have been used to synthesize such conjugated BODIPYs.

Synthesis and properties of meso-unsubstituted 3-pyrrolyl boron dipyrromethene.

We report the synthesis of meso-free 3-pyrrolyl boron dipyrrin (3-pyrrolyl BODIPY) and fully unsubstituted meso-free boron dipyrrin (parent BODIPY) in one pot under simple reaction conditions by treating meso-free dipyrromethane with pyrrole in CHCl3 followed by oxidation with DDQ, neutralization with triethylamine and complexation with BF3.OEt2. The compounds were separated by column chromatography on silica and isolated in 6-10 % yields.

Synthesis of sterically crowded polyarylated boron-dipyrromethenes.

A rapid synthetic route for polyarylated boron-dipyrromethenes using hexabromo boron-dipyrromethene as the key synthon is described. The X-ray structure revealed that the polyarylated BODIPY adopts a propeller-like conformation. These compounds exhibit red-shifted absorption and fluorescence bands with decent quantum yields and reversible oxidation and reduction waves when compared to unsubstituted boron-dipyrromethenes.