Synthesis and organic field effect transistor properties of isoindigo/DPP-based polymers containing a thermolabile group

Abstract

(E)-6,60 -Dibromo-1,1-bis(2-octyldodecyl)-(3,3 0 -biindolinylid-ene)-2,2 0 -dione and/or 2,5-bis(2-octyldodecyl)-3,6-di(5-bromothien-2-yl)pyrrolo [3,4-c]pyrrole-1,4-(2H,5H)-dione and their tBoc-counterparts were propagated with 2,5-bis(tributylstannyl)thiophene in a molar ratio of 0.8 : 0.2 : 1.0 to release P(ODIDT-BID), P(ODIDT$BDPP), P(ODDPPT$BID) and P(ODDPPT$BDPP) as a new series of random conjugated polymers (RCPs) bearing a large number of octyldodecyl chains to ensure solubility and a small number of thermocleavable tBoc function to cast H-bonding upon heating up to 220 C. All new polymers were synthesised via Pd catalysed Stille cross-coupling methodology in high yields and reasonable average molecular weights. The cast polymer films exhibited considerable red-shifted UV-vis absorption spectra and a further red-shift was also obtained in the thermal annealed films (at 220 C for 30 min), which reflected the increasing of crystalline structure. The formation of H-bonding in these polymers was investigated using X-ray diffractometry (XRD) measurements. The field-effect mobilities of these polymers were investigated in the configuration of bottom-gate and bottom-contact (BGBC) field-effect transistors (FETs). The results from FETs indicated that the crystalline structure of RCPs exhibited reasonable FET mobilities with 1.17 Â 10 À3 cm 2 V À1 s À1 for P(ODDPPT$BID) and 1.41 Â 10 À3 cm 2 V À1 s À1for P(ODDPPT$BDPP).

Inverting the Selectivity of the Newman–Kwart Rearrangement via One Electron Oxidation at Room Temperature

“…Moving onto amino analogues, we found that with a BOC protecting group as substituent (10), which is thermally labile, high yield was obtained. 22 With the N-acetyl group as substituent (11), full conversion to product was also observed. Finally, we found that S-(naphthalene-1-yl) dimethylcarbamothioate ( 12) could be obtained in high yields, while the 2-napthalene derivative 17 was not prone to the rearrangement.…”

“…Changing the methoxy group from the para - to the ortho -position high yield was retained affording 9 , while the meta -position ( 16 ) hampered the rearrangement. Moving onto amino analogues, we found that with a BOC protecting group as substituent ( 10 ), which is thermally labile, high yield was obtained . With the N- acetyl group as substituent ( 11 ), full conversion to product was also observed.…”

Peripherical thioester functionalization induces J-aggregation in bithiophene-DPP films and nanoparticles

“…The possibility to control the formation of H - or J -aggregates is a crucial aspect for the solid-state applications of DDPs. For instance, it has been reported that the increase in the DPP π–π stacking, with the consequent H -aggregation, improves carrier mobility in organic field-effect transistors 16 while, in bulk heterojunction solar cells, DPPs that generate H -aggregates display distinctly lower performances than those forming J -aggregates. 17 Furthermore, J -aggregates show NIR photoluminescence and they can be used as efficient solid state NIR emitters.…”

Green Solvent‐Processed Hemi‐Isoindigo Polymers for Stable Temperature Sensors

“…It has been reported that alkyl carbamates can be thermally decomposed at ≈100-150 °C. [53,54,[61][62][63] Therefore, the carbamate side chains in the HID polymers may be (partially) removed at 150 °C or a lower temperature to meet the processing temperature requirements of the PET substrate. The thermal decomposition behavior of PTEB, PMEB, PEEB, and PPEB was examined in more detail by using TGA at a constant temperature of 150 °C in air for 20 min.…”