Systematic elongation of thienyl linkers and their effect on optical and electrochemical properties in carbazole–BODIPY donor–acceptor systems

Abstract

(2016). Systematic elongation of thienyl linkers and their effect on optical and electrochemical properties in carbazole-BODIPY donor-acceptor systems. RSC Advances: an international journal to further the chemical sciences, 6 (43), 36500-36509.Systematic elongation of thienyl linkers and their effect on optical and electrochemical properties in carbazole-BODIPY donor-acceptor systems Abstract Synthesis, spectral and electrochemical properties of a series of new panchromatic BODIPY donor-acceptordonor derivatives, comprising carbazole conjugated with systematically elongated framework by thiophenebased linkers were investigated. It has been found that elongation of the π-system with one thiophene unit shifts the spectra toward near infrared, while incorporation of next thiophene derivatives has only limited influence on the lowest energy transition, causing no further shift of absorption maxima. Elongation of π-conjugation of the donor arm tunes the electron properties, influencing the ionization potential (IP) and electron affinity (EA) values of the molecules. The experimental results are supported by quantum chemical computations revealing that electron density of SOMO orbital is low at the 3-positions of terminal carbazole units in BODIPY push-pull oligomers while elongating their backbone, thus preventing them to undergo electrochemical polymerization giving reversibly p-and n-dopable products. Presented study tests the influence and limitations of incorporation of electron-rich substituents for designing panchromatic BODIPY systems. elongating their backbone, thus preventing them to undergo electrochemical polymerization giving reversibly p-and n-dopable products. Presented study tests the influence and limitations of incorporation of electron -rich substituents for designing panchromatic BODIPY systems.

Unprecedented Nucleophilic Attack of Piperidine on the Electron Acceptor during the Synthesis of Push‐Pull Dyes by a Knoevenagel Reaction

“…Notably, a red‐shift as high as 80 nm for PP2 and 70 nm for PP4 could be found, relative to PP1 and PP3 , respectively. This is consistent with an improvement of the electron‐donating ability of the electron donors by extending the π ‐conjugation …”

“…This is consistent with an improvement of the electron-donating ability of the electron donors by extending the π-conjugation. [26] As evidenced in the Figure 5, the highest occupied molecular orbital (HOMO) comprises both the dimethylaminobenzene group as well as the conjugated spacer. Conversely, the lowest unoccupied molecular orbital (LUMO) extends over the whole molecule.…”

The influence of driving force on intramolecular electron transfer: A theoretical study of subphthalocyanine‐AzaBODIPY‐C60 supramolecular triad

“…Usually, fullerenes are suitable acceptors due to their unique cage structure, high electron mobility, and excellence to accept electrons . In addition, there are many linkage units in D‐A materials, which are used as a bridge between donor and acceptor, such as porphyrins and azadipyrromethene (ADP) with conjugated rings . Noticeably, the absorption spectrum of ADP covers a range from 300 to 700 nm in the visible region, and it can also be excited in the near‐infrared region, which makes it a promising building block of solar cells …”

“…[22] In addition, there are many linkage units in D-A materials, which are used as a bridge between donor and acceptor, such as porphyrins and azadipyrromethene (ADP) with conjugated rings. [23,24] Noticeably, the absorption spectrum of ADP covers a range from 300 to 700 nm in the visible region, and it can also be excited in the nearinfrared region, which makes it a promising building block of solar cells. [25,26] Currently, a series of D-A photovoltaic materials have been synthesized based on subPC, ADP, and C 60 .…”

Facile synthesis of functional poly(vinylene sulfide)s containing donor–acceptor chromophores by a double click reaction

“…[1][2][3][4][5][6][7][8][9][10][11][12][13][14] In conjugated polymers, the sulfur-containing π-conjugated polymers are of particular scientific interest as they may create new functionalities that are difficult, if not impossible, to access by the polymers with pure carbon-based skeletons. [1][2][3][4][5][6][7][8][9][10][11][12][13][14] In conjugated polymers, the sulfur-containing π-conjugated polymers are of particular scientific interest as they may create new functionalities that are difficult, if not impossible, to access by the polymers with pure carbon-based skeletons.…”