4,7‐Diiodo‐2,1,3‐benzothiadiazole and 7,7′‐diiodo‐4,4′‐bi(2,1,3‐benzothiadiazole)

In the crystal structures of the title compounds, C₆H₂I₂N₂S, (I), and C₁₂H₄I₂N₄S₂, (II), respectively, a large number of short inter‐heteroatom contacts, such as S?N, I?I and N?I, are observed. In (II), which is non‐centrosymmetric, two halves of the mol­ecule are related by a crystallographic twofold axis.     

Synthesis, characterization and FET properties of novel dithiazolylbenzothiadiazole derivatives

Dithiazolylbenzothiadiazoles easily obtained have high electron affinity and the FET device of a trifluoromethylphenyl derivative exhibited a good n-type performance with high electron mobility.     

Cascade cyclization of aryldiynes using iodine: synthesis of iodo-substituted benzo[b]naphtho[2,1-d]thiophene derivatives for dye-sensitized solar cells

A facile, efficient, and general synthetic method for iodo-substituted benzo[b]naphtho[2,1-d]thiophenes has been developed via a cascade cyclization of thioanisole-substituted aryldiynes using iodine. A new donor–π linker–acceptor (D–π–A) organic dye, G1, with the benzo[b]naphtho[2,1-d]thiophene moiety as an electron donor has been synthesized, and the performance of dye-sensitized solar cell based on G1 has been investigated.     

4,7‐Bis(4‐pyridyl­ethynyl)‐2,1,3‐benzo­thia­diazo­le and its dipyridinium diperchlorate

The title compound, C₂₀H₁₀N₄S, and its dipyridinium salt, 4,4′‐(2,1,3‐benzo­diazol‐4,7‐diyl­diethynyl)­dipyridinium diperchlorate, C₂₀H₁₂N₄S²⁺·2ClO₄^?, display bond alternation in the 2,1,3‐benzo­thia­diazo­le rings, which suggests their quinonoid character. The dipyridinium dication mol­ecules stack along the a axis and form a dimer with short S?N interheteroatom contacts [3.146 (4) Å] between the two 1,2,5‐thia­diazo­le rings. The dimer is surrounded by the perchlorate anions with which it forms a large number of intermolecular N—H?O and C—H?O hydrogen bonds.     

Synthesis and characterization of new linear pi-conjugated molecules containing bis(ethynylpyridine) units with a benzothiadiazole spacer

Three novel 4,7-bis(n-pyridylethynyl)-2,1,3-benzothiadiazoles (n = 2, 3, and 4) were synthesized by using the Sonogashira cross-coupling reaction of 4,7-dibromo-2,1,3-benzothiadiazole with the corresponding ethynylpyridines in the presence of a Pd(II) catalyst. The viologen analogues were also prepared by methylation of pyridyl nitrogen atoms. X-ray structure analysis of these compounds revealed the linear molecular structures with unusual columnar crystal structures. Insertion of a benzothiadiazole moiety into the acetylene-pyridine skeleton brings about a large increase in electron affinity and the bispyridyl compounds obtained here show high fluorescence quantum yields.     

Functional 2-benzyl-1,2-dihydro[60]fullerenes as acceptors for organic photovoltaics: facile synthesis and high photovoltaic performances

A new series of functional 2-benzyl-1,2-dihydro[60]fullerenes, BnHCs, were synthesized efficiently via co-catalyzed selective monofunctionalization of C₆₀ with functional benzyl bromides. Photophysical and electrochemical properties of the new BnHCs were investigated. PSCs based on 2-MeO–4-CO₂Me–BnHC as new acceptor and P3HT as donor showed a power conversion efficiency of 3.75%, which is comparable to that of PC₆₁BM under the same device conditions.     

Unusual Hydrogen-bonding Networks Consisting of π-Extended 4,4′-Bipyridines and Chloranilic Acid

Hydrogen-bonding networks of π-extended 4,4′-bipyridines, 2,5-di(4-pyridyl)thiophene (1), 2,5-di(4-pyridyl)furan (2) and 1,4-di(4-pyridyl)benzene (3) with 2,5-dichloro-3,6-dihydroxy-1,4-benzoquinone (chloranilic acid, CA) have been investigated. The dipyridyl compounds afforded complexes 4 [(dication of 1)·(monoanion of CA)²], 5 [(dication of 2)·(dianion of CA)·(MeOH)] and 6 [(3)·(dication of 3)·(dianion of CA)·(H²O)⁶] with CA. X-ray structure analyses revealed the formation of unusual molecular tape and sheet structures involving N–H ?O, O–H ?O, C–H ?O and N–H ?N hydrogen bonds, where the aromatic spacer groups play an important role in constructing the unique crystal structures.     

A novel metal-free panchromatic TiO2 sensitizer based on a phenylenevinylene-conjugated unit and an indoline derivative for highly efficient dye-sensitized solar cells

A novel donor-π-spacer-acceptor type organic dye (AK01) bearing a phenylenevinylene-conjugated system and a derivative of indoline donor was synthesized for dye-sensitized solar cells. AK01 showed panchromatic TiO(2) sensitization with high overall conversion efficiency of 6.2% under AM 1.5 illumination (100 mW cm(-2)).     

Thieno[2,3-a]carbazole-based donor–π–acceptor organic dyes for efficient dye-sensitized solar cells

New donor–π–acceptor organic dyes K-1 and K-2 containing thieno[2,3-a]carbazole as an electron donor were designed and synthesized for dye-sensitized solar cells (DSCs). Photophysical and electrochemical properties of K-dyes were investigated. DSCs based on K-dyes showed a high conversion efficiency of 6.6–6.7% with a J_sc of 12.40–12.49 mA cm⁻² and a V_oc of 0.70–0.71 V. The molecular geometry calculation indicated that the existence of thienocarbazole donor in K-dyes enhanced the molecular planarity compared to the carbazole analogue dye MK-3. As a result, DSCs based on K-dyes showed high IPCEs, perhaps due to efficient intramolecular charge transfer and electron injection from excited dye to TiO₂ conduction band.     

Mechanical Motion in Crystals Triggered by Solid State Photochemical [2+2] Cycloaddition Reaction

Some special crystals respond to light by jumping, scattering or bursting just like popping of popcorn kernels on a hot surface. This rare phenomenon is called the photosalient (PS) effect. Molecular level control over the arrangement of light-responsive molecules in microscopic crystals for macroscale deformation or mechanical motion offers the possibility of using light to control smart material structures across the length scales. Photochemical [2+2] cycloaddition has recently emerged as a promising route to obtain photoswitchable structures and a wide variety of frameworks, but such reaction in crystals leading to macroscopic mechanical motion is relatively less explored. Study of chemistry of such novel soft crystals for the generation of smart materials is an imperative task. This minireview highlights recent advances in solid-state [2+2] cycloaddition in crystals to induce macroscale mechanical motion and thereby transduction of light into kinetic energy.