α,β-Unsubstitutedmeso-positioning thienyl BODIPY: a promising electron deficient building block for the development of near infrared (NIR) p-type donor–acceptor (D–A) conjugated polymers | Zendy

Benedetta Maria Squeo | Zendy; Vasilis G. Gregoriou | Zendy; Yang Han | Zendy; Alex PalmaCando | Zendy; Sybille Allard | Zendy; Efthymis Serpetzoglou | Zendy; Ioannis Konidakis | Zendy; Emmanuel Stratakis | Zendy; Apostolos Avgeropoulos | Zendy; Thomas D. Anthopoulos | Zendy; Martin Heeney | Zendy; Ullrich Scherf | Zendy; Christos L. Chochos | Zendy

Open Access

α,β-Unsubstitutedmeso-positioning thienyl BODIPY: a promising electron deficient building block for the development of near infrared (NIR) p-type donor–acceptor (D–A) conjugated polymers

Author(s) -

Benedetta Maria Squeo,

Vasilis G. Gregoriou,

Yang Han,

Alex PalmaCando,

Sybille Allard,

Efthymis Serpetzoglou,

Ioannis Konidakis,

Emmanuel Stratakis,

Apostolos Avgeropoulos,

Thomas D. Anthopoulos,

Martin Heeney,

Ullrich Scherf,

Christos L. Chochos

Publication year - 2018

Publication title -

journal of materials chemistry c

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.899

H-Index - 128

eISSN - 2050-7534

pISSN - 2050-7526

DOI - 10.1039/c7tc05900k

Subject(s) - conjugated system , materials science , polymer , electron acceptor , block (permutation group theory) , bodipy , electron , acceptor , infrared , photochemistry , band gap , electron donor , optoelectronics , fluorescence , chemistry , organic chemistry , optics , physics , condensed matter physics , catalysis , geometry , mathematics , quantum mechanics , composite material

It is demonstrated that α,β-unsubstituted meso-positioning thienyl BODIPY is an electron deficient unit that leads to the development of ultra low optical band gap (Eoptg < 1 eV) π-conjugated D–A quarterthiophene polymers. Furthermore, it is revealed that the optoelectronic, electrochemical and charge transporting properties of the resulting α,β-unsubstituted meso-positioning thienyl BODIPY quaterthiophene-based polymers are alkyl side chain positioning dependent. Tail-to-tail (TT) positioning of the alkyl side chains at the two central thiophenes of the quaterthiophene segment results in lower Eoptg, higher energy levels and increased hole mobility as compared to head-to-head (HH) positioning. Finally, even though the synthesized polymers exhibit high electron affinity, higher even than that of the fullerene derivative [6,6]-phenyl-C71-butyric acid methyl ester (PC71BM), they present only p-type behaviour in field effect transistors (FETs) independent of the alkyl side chain positioning.

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