Iodine(iii)-promoted regioselective and efficient synthesis of β-triazolyl BODIPYs for the selective recognition of nickel ions and bovine serum albumin

Abstract

Various ꞵ-triazolyl tethered BODIPYs were efficiently prepared in a sequential one-pot protocol involving the initial reaction of BODIPY with iodobenzene diacetate (IBD) and sodium azide to in situ generate BODIPY...

Dimethylaniline-Tetracyanobutadiene and Dimethylaniline-Extended-Tetracyanobutadiene Functionalized BODIPYs Witnessing Ultrafast Charge Transfer

“…The control compound C1 and the precursor 8-chloro BODIPY were synthesized by the reported procedure in good yields. 22 The BODIPY 1 was synthesized by the reaction of 8-chloro BODIPY with 4-ethynyl-N,N-dimethylaniline, using a catalytic amount of Pd(PPh 3 ) 2 Cl 2 in THF and TEA solvent at 0 °C for 2 h, in 80% yield. Similarly, BODIPY 2 was synthesized via the reaction of 8-chloro BODIPY with 4-((4-ethynylphenyl)ethynyl)-N,N-dimethylaniline, using a catalytic amount of Pd (PPh 3 ) 2 Cl 2 in THF and TEA solvent at 0 °C for 2 h, in 70% yield (Scheme 1).…”

“…The push–pull BODIPYs 3 and 4 were synthesized by the [2 + 2] CA-RE reaction of BODIPY 2 with strong acceptor TCNE and TCNQ units. The control compound C1 and the precursor 8-chloro BODIPY were synthesized by the reported procedure in good yields . The BODIPY 1 was synthesized by the reaction of 8-chloro BODIPY with 4-ethynyl- N,N -dimethylaniline, using a catalytic amount of Pd­(PPh 3 ) 2 Cl 2 in THF and TEA solvent at 0 °C for 2 h, in 80% yield.…”

“…π-Conjugated push–pull molecular systems have gained considerable interest in the scientific community due to their tunable optoelectronic properties and wide range of applications such as in organic field-effect transistors, nonlinear optics, photovoltaic devices, energy harvesting, bioimaging, sensors, and organic light-emitting diodes. − The optoelectronic properties and HOMO–LUMO gap of the π-conjugated chromophores can be altered by modifying the donor (D) or acceptor (A) unit or the π-linker between the D and A units. , 4,4-Difluoro-4-bora-3a,4a-diaza- s -indacene dyes, frequently known as BODIPY, have attracted a lot of attention in the last few decades because of their excellent chemical and photophysical properties including strong absorption, high fluorescence quantum yields and molar absorption coefficients, low toxicity, long fluorescence lifetime, as well as good photochemical stability. − The optoelectronic characteristics of the BODIPYs can be tuned by expanding the conjugation and incorporation of appropriate D/A groups at the meso and pyrrolic locations (α and β positions). − As a result, the BODIPY-based π-conjugated dyes have been extensively used in building fluorescent imaging agents, molecular switches, chemosensors, laser dyes, light-emitting devices, photosensitizers, and optoelectronic materials. − Noticeably, depending upon the peripheral substituents, the BODIPY unit can act as an electron donor or acceptor. − …”

BODIPY(aryl)iodonium salts in the efficient synthesis of diversely functionalized BODIPYs and selective detection of serum albumin

“…The BODIPY azide 5c could be a useful synthon in click chemistry to prepare 1,2,3-triazolyl appended BODIPYs. 50…”

“…The BODIPY azide 5c could be a useful synthon in click chemistry to prepare 1,2,3-triazolyl appended BODIPYs. 50 The copper(I) promoted reaction of 4a with phthalimide led to β-phthalimido appended BODIPY 5d in 56% yield. Under metal free conditions, the reaction of 4a with piperidine afforded β-piperidinyl BODIPY 5e in 58% yield.…”