Synthesis, Physical Properties, and Photocurrent Behavior of Strongly Emissive Boron‐Chelate Heterochrysene Derivatives

Abstract

A BPh2‐chelated heterochrysene derivative has been synthesized and characterized. Single crystal analysis of its analogous BF2 complex shows that all carbon and nitrogen atoms are almost in a plane, while the boron atoms twist out of this plane with a torsion angle of 28.796° measured between plane OBN and plane C1–C4–C4′. The BPh2 and BF2 compounds emit strong yellow and green light in methylene chloride with high fluorescence quantum yields, respectively. Thermogravimetric analysis results indicate that the thermal stability of both compounds is high. In addition, a photoswitching device was fabricated based on a thin film of the BF2 complex spin‐coated onto single‐walled carbon nanotubes, which produces a steady and reproducible photocurrent response.

Synthesis, Single Crystal, and Physical Properties of Asymmetrical Thiophene/Selenophene‐Fused Twistacenes

“…[12] Another strategyi st oi ncorporate the parents keletons with heteroatoms, [13] which can affect the crystal packing arrangementa nd tune the optoelectronic properties.F or example, the interplanar distance in chrysene single crystals is 5.07 , whereas its analogue, 6,6,13,13-tetrafluoro-6,13-dihydropyrido[1,2-c]pyrido-[1',2':3,4][1,3,2] oxazaborinino [6,5-e][1,3,2]oxazaborinine-7,14diium-6,13-diuide, has an average intermolecular distance of 3.30 . [14] Furthermore, aryl-substituted tetrathiaheptacenes possess chair conformations in contrast to planar heptacene. [15] Clearly, substitution of the CÀHm oiety in acenes with heteroatoms can produce electron-and hole-transporting materials.…”

Bottom-Up Synthesis of Nitrogen-Doped Polycyclic Aromatic Hydrocarbons

“…132,133 Moreover, the position and number of the B,N-coordinated unit in -expanded PAHs also affect the geometric and electronic structures. [134][135][136] Recently, we presented the synthesis of unique chromophores with triple B,N-coordinated units (Scheme 9). 137 Through a typical three-step reaction followed by the Buchwald-Hartwig reaction, hydrolysis, and cyclization, the key building block of 6,12,18-trichloro-5,11,17-triazatrinaphthylene (50) was obtained from 1,3,5-tribromobenzene.…”

Synthesis and Characterization of Alternating Polymers Incorporating Boron-Chelated Heterochrysene Units

“…The wavelengths of maximum absorption of BF 2 -poly (433 nm) and BPh 2 -poly (481 nm) were high compared to those of 1 and 2, because of the extended conjugation after polymerization. Otherwise, the relative electron-donating ability of the phenyl units can form an intramolecular charge-transfer system in D-p-A system, resulting in a significant difference between BF 2 -poly and BPh 2 -poly [26]. The biphenyl boron chelation in BPh 2 -poly resulted in a stronger bathochromic-shift.…”

“…Recently, our group reported the boron-chelated N,O-bidentate chrysene analogues in Scheme 1 [26]. As obtained two novel boron-based chrysene analogues (Compound 1 and 2) were synthesized by chelating with BF3·Et2O or BPh3, emitting strong green and yellow light in methylene chloride with high quantum yields.…”