TY - JOUR
T1 - Conjugated poly(azomethine)s via simple one-step polycondensation chemistry
T2 - Synthesis, thermal and optoelectronic properties
AU - Petrus, Michiel L.
AU - Bouwer, Ricardo K.M.
AU - Lafont, Ugo
AU - Murthy, D. H.K.
AU - Kist, René J.P.
AU - Böhm, Marcus L.
AU - Olivier, Yoann
AU - Savenije, Tom J.
AU - Siebbeles, Laurens D.A.
AU - Greenham, Neil C.
AU - Dingemans, Theo J.
PY - 2013/8/7
Y1 - 2013/8/7
N2 - Three conjugated triphenylamine-based poly(azomethine)s were prepared via well-known polycondensation chemistry using cheap and readily available starting materials and the results were contrasted with rrP3HT. Three functionalized diaminetriphenylamines (TPA(X), X = -H, -OMe, -CN) were polymerized in a simple one-step process with 2,3-dihydrothieno[3,4-b][1,4]dioxine-5,7-dicarbaldehyde (ThOx), with water being the only side product. The resulting polymers (TPA(X)ThOx, X = -H, -OMe, -CN) were characterized by GPC, IR and NMR, and show a good thermal stability. The opto-electronic properties could be tuned by changing the functionalization (X = -H, -OMe, -CN) on the triphenylamine moiety. Photovoltaic devices based on TPA(X)ThOx/PCBM (1:2) showed power conversion efficiencies in the range of 0.02-0.04%. TRMC measurements showed that the presence of PCBM as an electron acceptor facilitates the formation of free mobile charges after excitation of the polymer. The low device efficiencies are attributed to a low hole-mobility of the polymer in combination with poor active layer morphology.
AB - Three conjugated triphenylamine-based poly(azomethine)s were prepared via well-known polycondensation chemistry using cheap and readily available starting materials and the results were contrasted with rrP3HT. Three functionalized diaminetriphenylamines (TPA(X), X = -H, -OMe, -CN) were polymerized in a simple one-step process with 2,3-dihydrothieno[3,4-b][1,4]dioxine-5,7-dicarbaldehyde (ThOx), with water being the only side product. The resulting polymers (TPA(X)ThOx, X = -H, -OMe, -CN) were characterized by GPC, IR and NMR, and show a good thermal stability. The opto-electronic properties could be tuned by changing the functionalization (X = -H, -OMe, -CN) on the triphenylamine moiety. Photovoltaic devices based on TPA(X)ThOx/PCBM (1:2) showed power conversion efficiencies in the range of 0.02-0.04%. TRMC measurements showed that the presence of PCBM as an electron acceptor facilitates the formation of free mobile charges after excitation of the polymer. The low device efficiencies are attributed to a low hole-mobility of the polymer in combination with poor active layer morphology.
UR - http://www.scopus.com/inward/record.url?scp=84880019456&partnerID=8YFLogxK
U2 - 10.1039/c3py00433c
DO - 10.1039/c3py00433c
M3 - Article
AN - SCOPUS:84880019456
SN - 1759-9954
VL - 4
SP - 4182
EP - 4191
JO - Polymer Chemistry
JF - Polymer Chemistry
IS - 15
ER -
