The 100 m Robert C. Byrd Green Bank Telescope K-band (KFPA) receiver was used to perform a highsensitivity search for rotational emission lines from complex organic molecules in the cold interstellar medium towards TMC-1 (cyanopolyyne peak), focussing on the identification of new carbon-chain-bearing species as well as molecules of possible prebiotic relevance. We report a detection of the carbon-chain oxide species HC 7 O and derive a column density of (7.8 ± 0.9) × 10 11 cm −2 . This species is theorized to form as a result of associative electron detachment reactions between oxygen atoms and C 7 H − , and/or reaction of C 6 H 2 + with CO (followed by dissociative electron recombination). Upper limits are given for the related HC 6 O, C 6 O and C 7 O molecules. In addition, we obtained the first detections of emission from individual 13 C isotopologues of HC 7 N, and derive abundance ratios HC 7 N/HCCC 13 CCCCN = 110 ± 16 and HC 7 N/HCCCC 13 CCCN = 96 ± 11, indicative of significant 13 C depletion in this species relative to the local interstellar elemental 12 C/ 13 C ratio of 60-70. The observed spectral region covered two transitions of HC 11 N, but emission from this species was not detected, and the corresponding column density upper limit is 7.4 × 10 10 cm −2 (at 95% confidence). This is significantly lower than the value of 2.8 × 10 11 cm −2 previously claimed by Bell et al. (1997) and confirms the recent non-detection of HC 11 N in TMC-1 by Loomis et al. (2016). Upper limits were also obtained for the column densities of malononitrile and the nitrogen heterocycles quinoline, isoquinoline and pyrimidine.