We present a detailed characterization of three mixed stack organic semiconductors, where benzothienobenzothiophene electron donor is associated with fluorinesubstituted TCNQ of increasing electron affinity. BTBTTCNQ and BTBT-TCNQF2are isomorphous, whereas the three-dimensional packing of BTBT-TCNQF4is different. Rather surprisingly, we found that the degree of charge transfer is almost constant along the series, at variance with what has been found in analogous cocrystal series in which TCNQFxare involved. We explain this finding in terms of the Madelung energy resulting from interstack packing of the cocrystals, and of the fact that both the HOMO and HOMO-1 of BTBT are involved in the charge transfer mechanism. We also propose that the difference in interstack packing resulting from increasing F substitution is a consequence of electrostatic interactions.

Mixed stack organic semiconductors: The anomalous case of the BTBT-TCNQFx series / Castagnetti, Nicola; Girlando, Alberto; Masino, Matteo; Rizzoli, Corrado; Concepció Rovira, And. - In: CRYSTAL GROWTH & DESIGN. - ISSN 1528-7483. - 17:12(2017), pp. 6255-6261. [10.1021/acs.cgd.7b00852]

Mixed stack organic semiconductors: The anomalous case of the BTBT-TCNQFx series

Nicola Castagnetti;Alberto Girlando;Matteo Masino;Corrado Rizzoli;
2017

Abstract

We present a detailed characterization of three mixed stack organic semiconductors, where benzothienobenzothiophene electron donor is associated with fluorinesubstituted TCNQ of increasing electron affinity. BTBTTCNQ and BTBT-TCNQF2are isomorphous, whereas the three-dimensional packing of BTBT-TCNQF4is different. Rather surprisingly, we found that the degree of charge transfer is almost constant along the series, at variance with what has been found in analogous cocrystal series in which TCNQFxare involved. We explain this finding in terms of the Madelung energy resulting from interstack packing of the cocrystals, and of the fact that both the HOMO and HOMO-1 of BTBT are involved in the charge transfer mechanism. We also propose that the difference in interstack packing resulting from increasing F substitution is a consequence of electrostatic interactions.
Mixed stack organic semiconductors: The anomalous case of the BTBT-TCNQFx series / Castagnetti, Nicola; Girlando, Alberto; Masino, Matteo; Rizzoli, Corrado; Concepció Rovira, And. - In: CRYSTAL GROWTH & DESIGN. - ISSN 1528-7483. - 17:12(2017), pp. 6255-6261. [10.1021/acs.cgd.7b00852]
File in questo prodotto:
File Dimensione Formato  
BTBT-TQv3_rev (1).pdf

accesso aperto

Tipologia: Documento in Pre-print
Licenza: Creative commons
Dimensione 1.56 MB
Formato Adobe PDF
1.56 MB Adobe PDF Visualizza/Apri

I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.

Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11381/2852726
Citazioni
  • ???jsp.display-item.citation.pmc??? ND
  • Scopus 15
  • ???jsp.display-item.citation.isi??? 15
social impact