TY - JOUR

T1 - Methyl substituent effect on structure, luminescence and semiconducting properties of furan/phenylene co-oligomer single crystals

AU - Kazantsev, Maxim S.

AU - Beloborodova, Alina A.

AU - Frantseva, Ekaterina S.

AU - Rybalova, Tatyana V.

AU - Konstantinov, Vladislav G.

AU - Shundrina, Inna K.

AU - Paraschuk, Dmitry Yu

AU - Mostovich, Evgeny A.

PY - 2017/4/7

Y1 - 2017/4/7

N2 - Single crystals of furan/phenylene co-oligomers are among the most promising highly-emissive materials for applications in various optoelectronic devices. In this work, we synthesized and studied furan/phenylene co-oligomers with the same conjugated core 1,4-bis(5-phenylfuran-2-yl)benzene and methyl substituents at p- and m-positions of the terminal phenyls. The effect of substituents on the crystal packing, charge transport and luminescence of the single crystals was studied. Compared to the unsubstituted compound, the methyl-substituted co-oligomers demonstrated improved thermostability and enhanced photoluminescence, which we assign to J-aggregation resulting from the strong inclination of the molecules against the main crystal facet. The charge mobility in single crystal organic field-effect transistors decreased upon the inclination of the molecules. We conclude that the molecular tilt angle, intermolecular distances and interactions in crystals of heteroaryl-containing linear conjugated oligomers can be controlled by the introduction of end methyl groups in the appropriate positions.

AB - Single crystals of furan/phenylene co-oligomers are among the most promising highly-emissive materials for applications in various optoelectronic devices. In this work, we synthesized and studied furan/phenylene co-oligomers with the same conjugated core 1,4-bis(5-phenylfuran-2-yl)benzene and methyl substituents at p- and m-positions of the terminal phenyls. The effect of substituents on the crystal packing, charge transport and luminescence of the single crystals was studied. Compared to the unsubstituted compound, the methyl-substituted co-oligomers demonstrated improved thermostability and enhanced photoluminescence, which we assign to J-aggregation resulting from the strong inclination of the molecules against the main crystal facet. The charge mobility in single crystal organic field-effect transistors decreased upon the inclination of the molecules. We conclude that the molecular tilt angle, intermolecular distances and interactions in crystals of heteroaryl-containing linear conjugated oligomers can be controlled by the introduction of end methyl groups in the appropriate positions.

KW - FIELD-EFFECT TRANSISTORS

KW - SOLID-STATE ORDER

KW - PACKING

KW - DERIVATIVES

KW - EMISSION

KW - MOBILITY

KW - FILM

UR - http://www.scopus.com/inward/record.url?scp=85016400851&partnerID=8YFLogxK

U2 - 10.1039/c6ce02565j

DO - 10.1039/c6ce02565j

M3 - Article

AN - SCOPUS:85016400851

VL - 19

SP - 1809

EP - 1815

JO - CrystEngComm

JF - CrystEngComm

SN - 1466-8033

IS - 13

ER -