Highly Fluorescent Peri‐functionalized Perylenemonoimide Derivatives with Tunable Optical Properties for Selective Sensing of Electron‐rich Aromatic Amines

Abstract

A series of peri‐functionalized perylenemonoimide dyes containing an electron donating aromatic and polyaromatic group via Suzuki‐coupling reaction has been synthesized. Photophysical properties of the synthesized dyes are extensively investigated using various spectroscopic techniques. Introduction of substituent's at peri‐position shows a pronounced effect on emission properties. Electrochemical measurements suggest that the peri‐functionalization of perylenemonoimide dyes make reduction much more facile compared to unsubstituted dyes. Thereafter, an efficient and selective fluorescence quenching strategy via photo‐induced electron transfer process from electron‐rich aromatic amines to the synthesized dyes has been investigated.

Efficient Microwave‐Assisted Synthesis of Sonogashira‐Coupled Perylene Monoimide Derivatives: Impact of Electron‐Donating Groups on Optoelectronic Properties

“…Herein, we report a microwave‐assisted synthesis of 9‐bromo‐PMI 2 , Sonogashira‐coupled peri ‐functionalized PMI derivatives 3 and 6a – i (Scheme ), and alkynyl‐coupled electron‐rich aryl and polyaryl compounds 8c – g as precursors for 7c – g (see the Supporting Information) at reaction rates significantly faster than those for the conventional method. The optoelectronic properties of synthesized peri ‐functionalized PMIs 6a – i were extensively studied and compared with those of PMI derivative 6′ (see Figure ) prepared by Suzuki coupling …”

Perylene Monoimide as a Versatile Fluoroprobe: The Past, Present, and Future

“…The library of compounds including electron donating and polyaromatic group functionalized at peri-position of PMI were synthesized in good to excellent yield via two possible routes of Suzuki cross coupling (as shown in Figure 6). 29 In route 1, the mono-brominated PMI 11 was coupled with different boronic acid…”

“…Our group have utilized the electron-deficient nature of PMI to develop a sensor for electron-rich aromatic amines. 29 The photoinduced electron transfer (PET) from aromatic amine to PMI results in quenching of the fluorescence of PMI. We have synthesized a series of peri-functionalized PMI derivatives using Suzuki coupling reactions (vide supra) for sensing applications (see Figure 56).…”

“…The library of compounds including electron donating and polyaromatic group functionalized at the peri -position of PMI were synthesized in good to excellent yield via two possible routes of Suzuki cross-coupling (as shown in Figure 6 ). 29 In route 1, the mono-brominated PMI 11 was coupled with different boronic acid derivatives under Suzuki–Miyaura coupling conditions affording corresponding electron-donating and polyaromatic PMI derivatives 16 – 22 . On the other hand, in route 2, the synthesis of phenanthrene-conjugated PMI 23 was carried out in a slightly different way.…”

“…On the other hand, in route 2, the synthesis of phenanthrene conjugated PMI 23 was carried out in slightly different way. Firstly, the monobrominated PMI 11 was converted to functionalized boronic ester PMI-BE (15) followed by coupling with 9-bromo-phenanthrene using Suzuki-Miyaura coupling protocol 29. The two PMIs at peri-position can be coupled to each other via linker (such as Fluorine, Silafluorene and Carbazole) using Suzuki-Miyaura cross coupling reaction (as shown in Figure7) 30.…”