Activating intramolecular singlet exciton fission by altering π-bridge flexibility in perylene diimide trimers for organic solar cells

Abstract

In this study, two analogous perylene diimide (PDI) trimers, whose structures show rotatable single bond π−bridge connection (twisted) vs. rigid/fused π−bridge connection (planar), were synthesized and investigated. We show via...

Exploring a new class of singlet fission fluorene derivatives with high-energy triplets

“…7,8 Although this phenomenon has become a hot topic in chemical research, the families of SF capable materials remain relatively limited 9 and several mechanistic details of the SF process remain unclear. [10][11][12] Notably, the inuence of intramolecular charge transfer (ICT) on the SF has been the object of recent investigations carried out on dimers of tetracene, 13 pentacene, [14][15][16][17][18] terrylenediimide, [19][20][21][22][23] diketopyrrolopyrrole, [24][25][26][27][28] on tetracene and perylenediimide oligomers or dendrimers [29][30][31] and on push-pull polymers. [32][33][34] These studies generally consider either the effect of solvent polarity or the effect of tuning the electron donor/ acceptor group strength on the SF.…”

Controlled Fabrication and Characterization of Coronene Diimide‐Based Insoluble Thin Films Produced by Photoinduced Cyclization

“…This phenomenon brings high‐roughness and non‐continuous thin‐film structures which are inappropriate for use in organic devices. Therefore, this study focuses on Scholl type cyclization reactions for PDI derivative formation, particularly those induced by photoirradiation [54–65] . This reaction is accompanied by structural changes from a twisted structure to a structure comprised of π‐extended planar molecules, and proceeds without the release of gasses.…”

“…Therefore, this study focuses on Scholl type cyclization reactions for PDI derivative formation, particularly those induced by photoirradiation. [54][55][56][57][58][59][60][61][62][63][64][65] This reaction is accompanied by structural changes from a twisted structure to a structure comprised of π-extended planar molecules, and proceeds without the release of gasses. Because of this drastic change in molecular planarity, the solubility of the product may vary from that of the precursor.…”

Singlet Fission in Dideuterated Tetracene and Pentacene

“…For example, intramolecular vibrational modes between 300 and 1550 cm −1 have been found to be important for efficient SF in acenes [9,17,20,22–25] with a high sensitivity of SF rates to the frequency of the considered modes [17,22,25] and were found to induce vibronic coherences on timescales longer than the singlet fission process itself [19–21,26–28] . Intermolecular vibrations have been discussed as an additional contribution to charge transfer mediated SF via non‐adiabatic population transfer [11,20,28] and have been demonstrated to significantly affect SF rates and the subsequent triplet‐pair separation process [27,29–36] …”