Synthesis and characterization of novel symmetrical two-photon chromophores derived from bis(triphenylaminotetrathienoacenyl) and fused-thiophene units

Sureshraju Vegiraju, Yi You Liu, Kumaresan Prabakaran, Jen Shyang Ni, Yamuna Ezhumalai, Hsien Cheng Yu, Shueh Lin Yau, Jiann T. Lin, Ming Chou Chen, Tzu Chau Lin

Research output: Contribution to journalArticlepeer-review

7 Scopus citations

Abstract

Four new donor-π-donor (D-π121-D) fused-thiophene-based chromophores, end-functionalized with electron-donating triphenylamine (TPA) groups, were developed and characterized for a two-photon absorption study. Within this series, tetrathienoacene (thieno[2′,3′:4,5]thieno[3,2-b]thieno[2,3-d]thiophene; TTA) moieties were employed as side-conjugated (π1) units, and the central conjugated core (π2) units were altered with thiophene (T), bithiophene (bT), thienothiophene (TT), and dithienothiophene (DTT) for chromophores 1-4, respectively. The structural and photophysical relationships of the four compounds were compared, and all four chromophores showed strong fluorescence with good thermal stability. The energy gap compression of these chromophores was verified by electrochemistry and density functional theory (DFT) calculations. The two-photon-related properties of 1-4 were examined using femtosecond laser pulses as the probing tool. The magnitude of the two-photon absorptivity was found to be strongly dependent on the molecular conjugation length and the center fused-thiophene unit. Within the family, the most conjugated DTT-centered chromophore (4) exhibits the strongest and the most widely dispersed two-photon absorption cross-section value up to 3000 GM. To the best of our knowledge, this is the highest 2PA cross section value reported to date among the studied fused thiophene-based chromophores.

Original languageEnglish
Pages (from-to)54003-54010
Number of pages8
JournalRSC Advances
Volume5
Issue number67
DOIs
StatePublished - 2015

Fingerprint

Dive into the research topics of 'Synthesis and characterization of novel symmetrical two-photon chromophores derived from bis(triphenylaminotetrathienoacenyl) and fused-thiophene units'. Together they form a unique fingerprint.

Cite this