A quinacridone derivative with intensive emission in both solution and the solid state via a facile preparation for cell imaging applications

Abstract

tert-Butyloxycarbonyl (TBOC) substituted quinacridone (QA) derivative TBOC-QA was synthesized via a one-step simple chemical reaction and showed intense emission in both solution and the solid state.

N,N′-Substituted quinacridones for organic electronic device applications

“…Carbon based organic electronics in contrast to traditional electronics enable the fabrication of extremely flexible, highly conformable and even imperceptible electronic devices 7 . Such properties stimulate ground-breaking applications that may lead to new mainstream solutions in information and communication technology such as ambient intelligence for daily-life assistance 8,9 , soft robotics and actuators 10 , conformable and self-sustaining bioelectronic components for sports and recreation 11,12,13 , as well as imperceptible electronic platforms for surgical and diagnostic implants 14,15,16,17,18,19,20,21,22 . Materials that are easy to synthesize in high yield, at low cost 23 and that have widespread application as textile or cosmetic colors are very appealing for the development of sustainable organic electronic devices and integrated sensors 9,24,25 .…”

“…7 Such properties stimulate ground-breaking applications that may lead to new mainstream solutions in information and communication technology such as ambient intelligence for daily-life assistance, 8,9 soft robotics and actuators, 10 conformable and self-sustaining bioelectronic components for sports and recreation, [11][12][13] as well as imperceptible electronic platforms for surgical and diagnostic implants. [14][15][16][17][18][19][20][21][22] Materials that are easy to synthesize in high yield at low cost 23 and that have widespread application as textile or cosmetic colors are very appealing for the development of sustainable organic electronic devices and integrated sensors. 9,24,25 In our quest of investigating dyes and pigments of industrial relevance for organic semiconductors, we selected three molecules in the family of quinacridone pigments due to their straight forward synthesis and large-scale availability.…”

Conjugating Coumarin with Tetraphenylethylene to Achieve Dual‐State Emission for Reversible Mechanofluorochromism and Live Cell Imaging

“…In another example, Tian et al. reported quinacridone derivatives by attaching bulky tert‐butyloxycarbonyl units to weaken the ACQ effect, achieving intense emission in both solution and the solid state [12] . Alternatively, converting fluorophores into donor‐acceptor (D‐A)‐structured conjugates is also exploited to synthesize DSE emitters.…”

“…For example, DSEgens consisting of planar indoline and AIE-active tetraphenylethene (TPE)-triphenylamine were reported to exhibit DSE by Jing et al [11] In another example, Tian et al reported quinacridone derivatives by attaching bulky tertbutyloxycarbonyl units to weaken the ACQ effect, achieving intense emission in both solution and the solid state. [12] Alternatively, converting fluorophores into donor-acceptor (D-A)-structured conjugates is also exploited to synthesize DSE emitters. Harnessing 1,8-naphthalenimide as an electron acceptor and triphenylamine as an electron donor, Yu et al developed a series of DSE molecules and demonstrated their capability to fluorescently stain live cells.…”

D–A–D structured triphenylamine fluorophore with bright dual-state emission for reversible mechanofluorochromism and trace water detection

“…Fluorescent materials with high emission efficiency have attracted great attention due to their potential in applications such as chemo-/biosensors, mechanosensors, bioimaging, and organic light-emitting diodes (OLEDs). [1][2][3][4][5][6][7][8] The reported fluorescent materials mainly focus on aggregation-caused quenching (ACQ) and aggregation-induced emission (AIE) molecules. [9][10][11][12] Although ACQ molecules are highly emissive in dilute solutions, they are non-emissive or show weak emission in the solid state due to the nonradiative decay caused by the formation of detrimental aggregates.…”